Substituted arylketones

ABSTRACT

The invention relates to novel aryl ketones of the formula (I) 
                         
in which
         A 1 , A 2 , Q, R 1 , R 2 , X, Y and Z are as defined in the description,   their use as herbicides and processes and intermediates for their preparation.

The present invention relates to novel substituted aryl ketones, to aprocess for their preparation and to their use as plant treatmentagents, in particular as herbicides.

It is already known that certain substituted aryl ketones haveherbicidal properties (cf. EP-A-090 262, EP-A-135 191, EP-A-186 118,EP-A-186 119, EP-A-186 120, EP-A-319 075, EP-A-352 543, EP-A-418 175,EP-A-487 357, EP-A-527 036, EP-A-527 037, EP-A-560 483, EP-A-609 797,EP-A-609 798, EP-A-625 505, EP-A-625 508, EP-A-636 622, U.S. Pat. No. 5804 532, U.S. Pat. No. 5,834,402, U.S. Pat. No. 5,846,906, U.S. Pat. No.5,863,865, WO-A-95/31466, WO-A-96/26192, WO-A-96/26193, WO-A-96/26200,WO-A-96/26206, WO-A-97/27187, WO-A-97/35850, WO-A-97/41105,WO-A-97/41116, WO-A-97/41117, WO-A-97/41118, WO-A-97/43270,WO-A-97/46530, WO-A-98/28981, WO-A-98/31681, WO-A-98/31682,WO-A-99/03856, WO-A-99/07688, WO-A-99/07697, WO-A-99/10327,WO-A-99/10328, WO-A-00/05221 and in particular WO-A-00/21924). However,the activity of these compounds is not entirely satisfactory.

This invention, accordingly, provides the novel substituted aryl ketonesof the formula (I)

-   -   in which    -   A¹ represents a single bond or represents O (oxygen), S        (sulphur), SO or SO₂,    -   A² represents alkanediyl (alkylene), alkenediyl or alkinediyl,    -   Q represents O (oxygen) or S (sulphur),    -   R¹ represents hydrogen or represents in each case optionally        substituted alkyl, alkoxy, alkylthio, alkylsulphinyl,        alkylsulphonyl, alkylamino, dialkylamino, alkenyl, alkinyl,        cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, or represents        the grouping —C(Q)-R²,    -   R² represents hydrogen, amino, cyanoamino, nitroamino,        hydroxyamino, hydrazino, or represents in each case optionally        substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl,        alkylthio, alkylamino, dialkylamino, alkoxyamino,        N-alkyl-alkoxyamino, alkylhydrazino, dialkylhydrazino, alkenyl,        alkenyloxy, alkenylamino, alkenyloxyamino, alkinyl, alkinyloxy,        alkinylamino, cycloalkyl, cycloalkyloxy, cycloalkylamino,        cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylamino, aryl,        arylcarbonyl, aryloxy, aryloxycarbonyl, arylthio, arylamino,        arylhydrazino, arylalkyl, arylalkoxy, arylalkylthio,        arylalkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio,        heterocyclylamino, heterocyclylalkyl, heterocyclylalkoxy,        heterocyclylalkylthio or heterocyclylalkylamino,    -   X represents hydrogen, nitro, cyano, carboxyl, carbamoyl,        thiocarbamoyl, halogen, or represents in each case optionally        substituted alkyl, alkoxy, alkylthio, alkylsulphinyl,        alkylsulphonyl, alkylamino, dialkylamino or        dialkylaminosulphonyl,    -   Y represents hydrogen, nitro, cyano, carboxyl, carbamoyl,        thiocarbamoyl, halogen, or represents in each case optionally        substituted alkyl, alkoxy, alkylthio, alkylsulphinyl,        alkylsulphonyl, alkylamino, dialkylamino or        dialkylaminosulphonyl, and    -   Z represents one of the groupings below

-   -   -   where        -   m represents the numbers 0 to 6,        -   R³ represents hydrogen, halogen or represents in each case            optionally substituted alkyl, alkylthio or aryl, or—if m            represents 2—optionally also together with a second radical            R³ represents oxygen or alkanediyl (alkylene),        -   R⁴ represents hydroxyl, formyloxy, halogen, or represents in            each case optionally substituted alkoxy, alkylthio,            alkylsulphinyl, alkylsulphonyl, alkylcarbonyloxy,            alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylsulphonyloxy,            alkenyloxy, alkinyloxy, aryloxy, arylthio, arylsulphinyl,            arylsulphonyl, arylcarbonyloxy, arylcarbonylalkoxy,            arylsulphonyloxy, arylalkoxy, arylalkylthio,            arylalkylsulphinyl or arylalkylsulphonyl,        -   R⁵ represents hydrogen, cyano, carbamoyl, thiocarbamoyl,            halogen, or represents in each case optionally substituted            alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl,            alkoxycarbonyl or cycloalkyl,        -   R⁶ represents hydrogen or represents in each case optionally            substituted alkyl, alkenyl, alkinyl, cycloalkyl,            cycloalkylalkyl, aryl or arylalkyl,        -   R⁷ represents hydroxyl, formyloxy, or represents in each            case optionally substituted alkoxy, alkylcarbonyloxy,            alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylsulphonyloxy,            alkenyloxy, alkinyloxy, arylalkoxy, arylcarbonyloxy,            arylcarbonylalkoxy or arylsulphonyloxy,        -   R⁸ represents hydrogen, cyano, carbamoyl, thiocarbamoyl,            halogen, or represents in each case optionally substituted            alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio,            alkylsulphinyl or alkylsulphonyl,        -   R⁹ represents hydrogen or represents in each case optionally            substituted alkyl or cycloalkyl,        -   R¹⁰ represents hydrogen or represents in each case            optionally substituted alkyl or cycloalkyl, and        -   R¹¹ represents hydrogen, cyano, carbamoyl, halogen, or            represents in each case optionally substituted alkyl,            alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or            alkylsulphonyl.

The radical X is preferably located in position (2) of the phenyl ring.

In the definitions, the hydrocarbon chains, such as alkyl or alkanediyl,are in each case straight-chain or branched—including in combinationwith heteroatoms, such as in alkoxy.

If the compounds of the general formula (I) can exist in differentstereoisomeric forms, the invention includes the stereoisomeric formspossible in each case.

Preferred substituents or ranges of the radicals present in the formulaelisted above and below are defined below.

-   -   A¹ preferably represents O or represents a single bond.    -   A² preferably represents alkanediyl (alkylene), alkenediyl or        alkinediyl having in each case up to 6 carbon atoms.    -   Q preferably represents O (oxygen).    -   R¹ preferably represents hydrogen, represents in each case        optionally cyano-, halogen-, C₁–C₄-alkoxy-, C₁–C₄-alkylthio-,        C₁–C₄-alkyl-sulphinyl- or C₁–C₄-alkylsulphonyl-substituted        alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or        alkylamino having in each case 1 to 6 carbon atoms in the alkyl        groups, represents dialkylamino having in each case 1 to 4        carbon atoms in the alkyl groups, represents in each case        optionally cyano- or halogen-substituted alkenyl or alkinyl        having in each case 2 to 6 carbon atoms, represents in each case        optionally cyano-, halogen- or C₁–C₄-alkyl-substituted        cycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon        atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms        in the alkyl moiety, represents in each case optionally nitro-,        cyano-, halogen-, C₁–C₄-alkyl-, C₁–C₄-halogenoalkyl-,        C₁–C₄-alkoxy- or C₁–C₄-halogeno-alkoxy-substituted aryl or        arylalkyl having in each case 6 or 10 carbon atoms in the aryl        group and optionally 1 to 4 carbon atoms in the alkyl moiety, or        represents the grouping —C(Q)-R².    -   R² preferably represents hydrogen, amino, cyanoamino,        nitroamino, hydroxyamino, hydrazino, represents        C₁–C₄-alkylcarbonyl, represents C₁–C₄-alkoxy-carbonyl,        represents in each case optionally cyano-, halogen-,        C₁–C₄-alkoxy-, C₁–C₄-alkylthio-, C₁–C₄-alkylsulphinyl- or        C₁–C₄-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio,        alkylamino, alkoxyamino or alkylhydrazino having in each case 1        to 6 carbon atoms in the alkyl groups, represents dialkylamino,        N-alkyl-alkoxy-amino or dialkylhydrazino having in each case 1        to 4 carbon atoms in the alkyl groups, represents in each case        optionally halogen-substituted alkenyl, alkenyloxy,        alkenylamino, alkenyloxyamino, alkinyl, alkinyloxy or        alkinylamino having in each case 2 to 6 carbon atoms, represents        in each case optionally cyano-, halogen- or        C₁–C₄-alkyl-substituted cycloalkyl, cycloalkyloxy,        cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy or        cycloalkylalkylamino having in each case 3 to 6 carbon atoms in        the cycloalkyl group and optionally 1 to 4 carbon atoms in the        alkyl moiety, represents in each case optionally nitro-, cyano-,        halogen-, C₁–C₄-alkyl-, C₁–C₄-halogenoalkyl-, C₁–C₄-alkoxy-,        C₁–C₄-halogenoalkoxy- or C₁–C₄-alkoxy-carbonyl-substituted aryl,        arylcarbonyl, aryloxy, aryloxycarbonyl, arylthio, arylamino,        arylhydrazino, arylalkyl, arylalkoxy, arylalkylthio or        arylalkylamino having in each case 6 or 10 carbon atoms in the        aryl group and optionally 1 to 4 carbon atoms in the alkyl        moiety, or represents in each case optionally nitro-, cyano-,        halogen-, C₁–C₄-alkyl-, C₁–C₄-halogenoalkyl-, C₁–C₄-alkoxy-,        C₁–C₄-halogenoalkoxy-, C₁–C₄-alkylthio-,        C₁–C₄-halogenoalkylthio- or C₁–C₄-alkoxy-carbonyl-substituted        monocyclic or bicyclic heterocyclyl, heterocyclyloxy,        heterocyclylthio, heterocyclylamino, heterocyclylalkyl,        heterocyclylalkoxy, heterocyclylalkylthio or        heterocyclylalkylamino, where in each case the heterocyclyl        grouping contains up to 10 carbon atoms and additionally at        least one heteroatom selected from the group consisting of        nitrogen (N) (but at most 5 N atoms), oxygen (O) (but at most 2        O atoms), sulphur (S) (but at most 2 S atoms), SO and SO₂ and        also optionally additionally one group selected from the group        consisting of oxo (C═O), thioxo (C═S), imino (C═NH), cyanoimino        (C═N—CN) and nitroimino (C═N—NO₂).    -   X preferably represents hydrogen, nitro, cyano, carboxyl,        carbamoyl, thiocarbamoyl, halogen, or represents in each case        optionally cyano-, halogen-, C₁–C₄-alkoxy-, C₁–C₄-alkylthio-,        C₁-C₄-alkylsulphinyl- or C₁–C₄-alkylsulphonyl-substituted alkyl,        alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino,        dialkylamino or dialkylaminosulphonyl having in each case 1 to 6        carbon atoms in the alkyl groups.    -   Y preferably represents hydrogen, nitro, cyano, carboxyl,        carbamoyl, thiocarbamoyl, halogen, or represents in each case        optionally cyano-, halogen-, C₁–C₄-alkoxy-, C₁–C₄-alkylthio-,        C₁–C₄-alkylsulphinyl- or C₁–C₄-alkylsulphonyl-substituted alkyl,        alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino,        dialkylamino or dialkylaminosulphonyl having in each case 1 to 6        carbon atoms in the alkyl groups.    -   Z preferably represents one of the groupings below.

-   -   m preferably represents the numbers 0 to 3.    -   R³ preferably represents hydrogen, halogen, represents in each        case optionally cyano-, halogen-, C₁–C₄-alkoxy-,        C₁–C₄-alkylthio-, C₁–C₄-alkylsulphinyl- or        C₁–C₄-alkylsulphonyl-substituted alkyl or alkylthio having in        each case 1 to 6 carbon atoms, or represents phenyl, or if m        represents 2—optionally also together with a second radical R³        represents oxygen or alkanediyl (alkylene) having 3 to 5 carbon        atoms.    -   R⁴ preferably represents hydroxyl, formyloxy, halogen,        represents in each case optionally cyano-, halogen-,        C₁–C₄-alkoxy-, C₁–C₄-alkylthio-, C₁–C₄-alkylsulphinyl- or        C₁–C₄-alkylsulphonyl-substituted alkoxy, alkylthio,        alkylsulphinyl, alkylsulphonyl, alkylcarbonyloxy,        alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulphonyloxy        having in each case 1 to 6 carbon atoms, represents in each case        optionally halogen-substituted alkenyloxy or alkinyloxy having        in each case 3 to 6 carbon atoms, represents in each case        optionally nitro-, cyano-, halogen-, C₁–C₄-alkyl-,        C₁–C₄-halogenoalkyl-, C₁–C₄-alkoxy-, C₁–C₄-halogenoalkoxy-,        C₁–C₄-alkylthio-, C₁–C₄-halogenoalkylthio-,        C₁–C₄-alkylsulphinyl-, C₁–C₄-halogenoalkylsulphinyl-,        C₁–C₄-alkylsulphonyl- or        C₁–C₄-halogenoalkylsulphonyl-substituted aryloxy, arylthio,        arylsulphinyl, arylsulphonyl, arylcarbonyloxy,        arylcarbonylalkoxy, arylsulphonyloxy, arylalkoxy, arylalkylthio,        arylalkylsulphinyl or arylalkylsulphonyl having in each case 6        or 10 carbon atoms in the aryl group and optionally 1 to 4        carbon atoms in the alkyl moiety.    -   R⁵ preferably represents hydrogen, cyano, carbamoyl,        thiocarbamoyl, halogen, represents in each case optionally        cyano-, halogen-, C₁–C₄-alkoxy-, C₁–C₄-alkylthio-,        C₁–C₄-alkylsulphinyl- or C₁–C₄-alkylsulphonyl-substituted alkyl,        alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or        alkoxycarbonyl having in each case 1 to 6 carbon atoms in the        alkyl groups or represents optionally cyano-, halogen- or        C₁–C₄-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms.    -   R⁶ preferably represents hydrogen, represents optionally cyano-,        halogen-, C₁–C₄-alkoxy-, C₁–C₄-alkylthio-, C₁–C₄-alkylsulphinyl-        or C₁–C₄-alkylsulphonyl-substituted alkyl having 1 to 6 carbon        atoms, represents in each case optionally cyano- or        halogen-substituted alkenyl or alkinyl having in each case 3 to        6 carbon atoms, represents in each case optionally cyano-,        halogen- or C₁–C₄-alkyl-substituted cycloalkyl or        cycloalkylalkyl having in each case 3 to 6 carbon atoms in the        cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl        moiety, or represents in each case optionally nitro-, cyano-,        halogen-, C₁–C₄-alkyl-, C₁–C₄-halogenoalkyl-, C₁–C₄-alkoxy-,        C₁–C₄-halogenoalkoxy-, C₁–C₄-alkylthio-,        C₁–C₄-halogenoalkylthio-, C₁–C₄-alkylsulphinyl-,        C₁–C₄-halogenoalkylsulphinyl-, C₁–C₄-alkylsulphonyl- or        C₁–C₄-halogenoalkylsulphonyl-substituted aryl or arylalkyl        having in each case 6 or 10 carbon atoms in the aryl group and        optionally 1 to 4 carbon atoms in the alkyl moiety.    -   R⁷ preferably represents hydroxyl, formyloxy, represents in each        case optionally cyano-, halogen- or C₁–C₄-alkoxy-substituted        alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy,        alkylaminocarbonyloxy or alkylsulphonyloxy having in each case 1        to 6 carbon atoms in the alkyl groups, represents in each case        optionally cyano-, or halogen-substituted alkenyloxy or        alkinyloxy having in each case 3 to 6 carbon atoms, or        represents in each case optionally nitro-, cyano-, halogen-,        C₁–C₄-alkyl-, C₁–C₄-halogenoalkyl-, C₁–C₄-alkoxy-,        C₁–C₄-halogenoalkoxy-, C₁–C₄-alkylthio-,        C₁–C₄-halogenoalkylthio-, C₁–C₄-alkylsulphinyl-,        C₁–C₄-halogenoalkylsulphinyl-, C₁–C₄-alkylsulphonyl- or        C₁–C₄-halogenoalkylsulphonyl-substituted arylalkoxy,        arylcarbonyloxy, arylcarbonylalkoxy or arylsulphonyloxy having        in each case 6 or 10 carbon atoms in the aryl group and        optionally 1 to 4 carbon atoms in the alkyl moiety.    -   R⁸ preferably represents hydrogen, cyano, carbamoyl,        thiocarbamoyl, halogen, or represents in each case optionally        cyano-, halogen- or C₁–C₄-alkoxy-substituted alkyl,        alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl        or alkylsulphonyl having in each case 1 to 6 carbon atoms in the        alkyl groups.    -   R⁹ preferably represents hydrogen, represents optionally cyano-,        halogen- or C₁–C₄-alkoxy-substituted alkyl, or represents        optionally cyano-, halogen- or C₁–C₄-alkyl-substituted        cycloalkyl having 3 to 6 carbon atoms.    -   R¹⁰ preferably represents hydrogen, represents optionally        cyano-, halogen- or C₁–C₄-alkoxy-substituted alkyl, or        represents optionally cyano-, halogen- or        C₁–C₄-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms.    -   R¹¹ preferably represents hydrogen, cyano, carbamoyl, halogen,        or represents in each case optionally cyano-, halogen- or        C₁–C₄-alkoxy-substituted alkyl, alkoxy, alkoxycarbonyl,        alkylthio, alkylsulphinyl or alkylsulphonyl having in each case        1 to 6 carbon atoms in the alkyl groups.    -   A² particularly preferably represents methylene (—CH₂—),        ethane-1,1-diyl (—CH(CH₃)—), ethane-1,2-diyl (dimethylene,        —CH₂CH₂—), propane-1,1-diyl (—CH(C₂H₅)—), propane-1,2-diyl        (—CH(CH₃)CH₂—), propane-1,3-diyl (—CH₂CH₂CH₂—), butane-1,3-diyl        (—CH(CH₃)CH₂CH₂—), butane-1,4-diyl (—CH₂CH₂CH₂CH₂—), ethenediyl,        propenediyl, butenediyl, ethinediyl, propinediyl or butinediyl.    -   R¹ particularly preferably represents hydrogen, represents in        each case optionally cyano-, fluorine-, chlorine-, bromine-,        methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n-        or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, n- or        i-propylsulphinyl-, methylsulphonyl- or        ethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-,        i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n-        or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n-        or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl,        ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl,        ethylsulphonyl, methylamino, ethylamino, n- or i-propylamino,        n-, i-, s- or t-butylamino, represents dimethylamino or        diethylamino, represents in each case optionally fluorine-,        chlorine- and/or bromine-substituted ethenyl, propenyl, butenyl,        pentenyl, ethinyl, propinyl, butinyl or pentinyl, represents in        each case optionally cyano-, fluorine-, chlorine-, bromine-,        methyl-, ethyl- or propyl-substituted cyclopropyl, cyclobutyl,        cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl,        cyclopentylmethyl or cyclohexylmethyl, or represents in each        case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-,        methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-,        trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,        di-fluoromethoxy- or trifluoromethoxy-substituted phenyl,        naphthyl, phenylmethyl, phenylethyl, naphthylmethyl or        naphthylethyl or represents the grouping —C(Q)-R².    -   R² particularly preferably represents hydrogen, amino,        cyanoamino, nitroamino, hydroxyamino, hydrazino, represents in        each case optionally cyano-, fluorine-, chlorine-, methoxy-,        ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or        i-propylthio-, methylsulphinyl-, ethylsulphinyl-, n- or        i-propylsulphinyl-, methylsulphonyl- or        ethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-,        i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n-        or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n-        or i-propylthio, n-, i-, s- or t-butylthio, methylamino,        ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino,        methoxyamino, ethoxyamino, n- or i-propoxyamino, n-, i-, s- or        t-butoxyamino, methylhydrazino, ethylhydrazino, n- or        i-propylhydrazino, n-, i-, s- or t-butylhydrazino, represents        dimethylamino, diethylamino, N-methyl-methoxyamino,        dimethylhydrazino or diethylhydrazino, represents in each case        optionally fluorine-, chlorine- and/or bromine-substituted        ethenyl, propenyl, butenyl, pentenyl, ethinyl, propinyl,        butinyl, pentinyl, propenyloxy, butenyloxy, pentenyloxy,        propenylthio, butenylthio, pentenylthio, propenylamino,        butenylamino, pentenylamino, propenyloxyamino, butenyloxyamino,        pentenyloxyamino, ethinyl, propinyl, butinyl, pentinyl,        propinyloxy, butinyloxy, pentinyloxy, propinylamino,        butinylamino or pentinylamino, represents in each case        optionally cyano-, fluorine-, chlorine-, bromine-, methyl-,        ethyl- or propyl-substituted cyclopropyl, cyclobutyl,        cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy,        cyclopentyloxy, cyclohexyloxy, cyclopropylamino,        cyclobutylamino, cyclopentylamino, cyclohexylamino,        cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,        cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy,        cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylamino,        cyclobutylmethylamino, cyclopentylmethylamino or        cyclohexylmethylamino, represents in each case optionally        nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-,        n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-,        methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-,        trifluoromethoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- or        i-propoxycarbonyl-substituted phenyl, phenylcarbonyl, phenoxy,        phenoxycarbonyl, phenylthio, phenylamino, phenylhydrazino,        naphthyl, naphthyloxy, naphtylthio, naphthylamino, phenylmethyl,        phenylethyl, phenylmethoxy, phenylethoxy, phenylmethylthio,        phenylethylthio, phenylmethylamino, phenylethylamino,        naphthylmethyl, naphthylethyl, naphthylmethoxy, naphthylethoxy,        naphthylmethylamino or naphthylethylamino, or represents in each        case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-,        methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-,        difluoromethyl-, trifluoromethyl-, dichloromethyl-,        trichloromethyl-, chlorodifluoromethyl-, fluorodichloromethyl-,        methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-,        difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n-        or i-propylthio-, n-, i-, s- or t-butylthio-,        difluoromethylthio-, trifluoromethylthio-, methoxycarbonyl-,        ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted monocyclic        or bicyclic heterocyclyl, heterocyclyloxy, heterocyclylamino,        heterocyclylalkyl, heterocyclylalkoxy or heterocyclylalkylamino        from the group consisting of furyl, furyloxy, furylamino,        furylmethyl, furylmethoxy, furylmethylamino, thienyl,        thienylmethyl, pyrrolidinyl, pyrrolidinylamino, oxopyrrolidinyl,        pyrrolyl, indolyl, pyrrolylmethyl, pyrazolyl, pyrazolyloxy,        pyrazolylamino, pyrazolylmethyl, imidazolyl, imidazolylmethyl,        2-oxo-1,3-diaza-cyclopentyl, oxazolyl, dihydrooxazolyl        (oxazolinyl), isoxazolyl, dihydroisoxazolyl (isoxazolinyl),        tetrahydroisoxazolyl (isoxazolidinyl), oxazolylmethyl,        thiazolyl, dihydrothiazolyl (thiazolinyl), tetrahydrothiazolyl        (thiazolidinyl), thiazolylmethyl, thiazolidinyl,        oxothiazolidinyl, cyanoiminothiazolidinyl, oxotriazolinyl,        oxotetrazolinyl, piperidinyl, piperidinylamino, oxopiperidinyl,        2-oxo-1,3-diaza-cyclohexyl, 2-oxo-1-aza-cycloheptyl,        2-oxo-1,3-diazacycloheptyl, morpholinyl, morpholinylamino,        piperazinyl, pyridinyl, pyridinyloxy, pyridinylamino,        pyridinylmethyl, pyridinylmethoxy, pyrimidinyl, pyrimidinyloxy,        pyrimidinylmethyl, pyrimidinylmethoxy.    -   X particularly preferably represents hydrogen, nitro, cyano,        carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine,        iodine, or represents in each case optionally cyano-, fluorine-,        chlorine-, methoxy-, ethoxy-, methylthio-, ethylthio-,        methylsulphinyl-, ethylsulphinyl-, methylsulphonyl- or        ethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-,        i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s-        or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-,        s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or        i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or        i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino,        n-, i-, s- or t-butylamino, dimethylamino, diethylamino,        dimethylaminosulphonyl or diethylaminosulphonyl.    -   Y particularly preferably represents hydrogen, nitro, cyano,        carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine,        iodine, or represents in each case optionally cyano-, fluorine-,        chlorine-, methoxy-, ethoxy-, methylthio-, ethylthio-,        methylsulphinyl-, ethylsulphinyl-, methylsulphonyl- or        ethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-,        i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s-        or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-,        s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or        i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or        i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino,        n-, i-, s- or t-butylamino, dimethylamino, diethylamino,        dimethylaminosulphonyl or diethylaminosulphonyl.    -   m particularly preferably represents the number 0, 1 or 2.    -   R³ particularly preferably represents hydrogen, fluorine,        chlorine or bromine, represents in each case optionally cyano-,        fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-,        methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-,        ethylsulphinyl-, methylsulphonyl- or ethylsulphonyl-substituted        methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,        methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or        t-butylthio, or represents phenyl, or—if m represents 2,        —optionally also together with a second radical R³ represents        oxygen, propane-1,3-diyl or butane-1,4-diyl.    -   R⁴ particularly preferably represents hydroxyl, formyloxy,        fluorine or chlorine, represents in each case optionally cyano-,        fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-,        methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-,        ethylsulphinyl-, methylsulphonyl- or ethylsulphonyl-substituted        methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or        i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl,        ethylsulphonyl, acetyloxy, propionyloxy, n- or i-butyroyloxy,        methoxycarbonyloxy, ethoxycarbonyloxy, n- or        i-propoxycarbonyloxy, methylaminocarbonyloxy,        ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy,        methylsulphonyloxy, ethylsulphonyloxy, n- or        i-propylsulphonyloxy, represents in each case optionally        fluorine-, chlorine- and/or bromine-substituted propenyloxy,        butenyloxy, propinyloxy or butinyloxy, represents in each case        optionally nitro-, cyano-, fluorine-, chlorine-, bromine-,        methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-,        trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,        difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n-        or i-propylthio-, difluoromethylthio-, trifluoromethylthio-,        methylsulphinyl-, ethylsulphinyl-, trifluoromethylsulphinyl-,        methylsulphonyl-, ethylsulphonyl- or        trifluoromethylsulphonyl-substituted phenyloxy, phenylthio,        phenylsulphinyl, phenylsulphonyl, phenylcarbonyloxy,        phenylcarbonylalkoxy, phenylsulphonyloxy, phenylmethoxy,        phenylmethylthio, phenylmethylsulphinyl or        phenylmethylsulphonyl.    -   R⁵ particularly preferably represents hydrogen, cyano,        carbamoyl, thiocarbamoyl, fluorine, chlorine or bromine,        represents in each case optionally cyano-, fluorine-, chlorine-,        methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n-        or i-propylthio-, methylsulphinyl-, ethylsulphinyl-,        methylsulphonyl- or ethylsulphonyl-substituted methyl, ethyl, n-        or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or        i-propoxy, methylthio, ethylthio, n- or i-propylthio,        methylsulphinyl, ethylsulphinyl, methylsulphonyl,        ethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, n- or        i-propoxycarbonyl, or represents in each case optionally cyano-,        fluorine-, chlorine-, methyl- or ethyl-substituted cyclopropyl,        cyclobutyl, cyclopentyl or cyclohexyl.    -   R⁶ particularly preferably represents hydrogen, represents in        each case optionally cyano-, fluorine-, chlorine-, methoxy-,        ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or        i-propylthio-, methylsulphinyl-, ethylsulphinyl-,        methylsulphonyl- or ethylsulphonyl-substituted methyl, ethyl, n-        or i-propyl, n-, i-, s- or t-butyl, represents in each case        optionally cyano-, fluorine-, chlorine- or bromine-substituted        propenyl, butenyl, propinyl or butinyl, represents in each case        optionally cyano-, fluorine-, chlorine-, methyl- or        ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl,        cyclohexyl, cyclopropylmethyl, cyclobutylmethyl,        cyclopentylmethyl or cyclohexylmethyl, or represents in each        case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-,        methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-,        trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,        difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n-        or i-propylthio-, n-, i-, s- or t-butylthio-,        difluoromethylthio-, trifluoromethylthio-, methylsulphinyl-,        ethylsulphinyl-, trifluoromethylsulphinyl-, methylsulphonyl,        ethylsulphonyl- or trifluoromethylsulphonyl-substituted phenyl        or phenylmethyl.    -   R⁷ particularly preferably represents hydroxyl, formyloxy,        represents in each case optionally cyano-, fluorine-, chlorine-,        methoxy-, ethoxy-, n- or i-propoxy-substituted methoxy, ethoxy,        n- or i-propoxy, acetyloxy, propionyloxy, n- or i-butyroyloxy,        methoxycarbonyloxy, ethoxycarbonyloxy, n- or        i-propoxycarbonyloxy, methylaminocarbonyloxy,        ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy,        methylsulphonyloxy, ethylsulphonyloxy, n- or        i-propylsulphonyloxy, or represents in each case optionally        cyano-, fluorine-, chlorine- or bromine-substituted propenyloxy,        butenyloxy, propinyloxy or butinyloxy, or represents in each        case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-,        methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-,        trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,        difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n-        or i-propylthio-, difluoromethylthio-, trifluoromethylthio-,        methylsulphinyl-, ethylsulphinyl-, trifluoromethylsulphinyl-,        methylsulphonyl-, ethylsulphonyl- or        trifluoromethylsulphonyl-substituted phenylmethoxy,        phenylcarbonyloxy, phenylcarbonylmethoxy or phenylsulphonyloxy.    -   R⁸ particularly preferably represents hydrogen, cyano,        carbamoyl, thiocarbamoyl, fluorine, chlorine or bromine, or        represents in each case optionally cyano-, fluorine-, chlorine-,        methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n-        or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or        i-butyroyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl,        ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio,        n- or i-propylthio, methylsulphinyl, ethylsulphinyl,        methylsulphonyl or ethylsulphonyl.    -   R⁹ particularly preferably represents hydrogen, represents in        each case optionally cyano-, fluorine-, chlorine-, methoxy-,        ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or        i-propyl, n-, i-, s- or t-butyl, or represents in each case        optionally cyano-, fluorine-, chlorine-, methyl- or        ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or        cyclohexyl.    -   R¹⁰ particularly preferably represents hydrogen, represents in        each case optionally cyano-, fluorine-, chlorine-, methoxy-,        ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or        i-propyl, n-, i-, s- or t-butyl, or represents in each case        optionally cyano-, fluorine-, chlorine-, methyl- or        ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or        cyclohexyl.    -   R¹¹ particularly preferably represents hydrogen, cyano,        carbamoyl, fluorine, chlorine or bromine or represents in each        case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-,        n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-,        i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,        methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,        methylthio, ethylthio, n- or i-propylthio, methylsulphinyl,        ethylsulphinyl, methylsulphonyl or ethylsulphonyl.    -   A² very particularly preferably represents methylene (—CH₂—),        ethane-1,2-diyl (dimethylene, —CH₂CH₂—) or propane-1,3-diyl        (—CH₂CH₂CH₂—).    -   R¹ very particularly preferably represents hydrogen, represents        in each case optionally cyano-, fluorine-, chlorine-, methoxy-,        ethoxy-, methylthio-, ethylthio-, methylsulphinyl-,        ethylsulphinyl-, methylsulphonyl- or ethylsulphonyl-substituted        methyl, ethyl, n- or i-propyl, n- or i-butyl, represents        methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or        i-propylthio, methylamino, ethylamino, n- or i-propylamino,        represents dimethylamino, represents in each case optionally        fluorine- and/or chlorine-substituted propenyl, butenyl,        ethinyl, propinyl or butinyl, represents in each case optionally        cyano-, fluorine-, chlorine- or methyl-substituted cyclopropyl,        cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl,        cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or        represents in each case optionally nitro-, cyano-, fluorine-,        chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-,        s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or        i-propoxy-, difluoromethoxy- or trifluoromethoxy-substituted        phenyl, phenylmethyl or phenylethyl, or represents the grouping        —C(Q)-R².    -   R² very particularly preferably represents hydrogen, amino,        hydroxyamino, hydrazino, represents in each case optionally        cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or        i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,        methylsulphinyl-, ethylsulphinyl-, methylsulphonyl- or        ethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-,        i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio,        ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or        i-propylamino, methoxyamino, ethoxyamino, n- or i-propoxyamino,        represents dimethylamino, represents N-methyl-methoxyamino,        represents dimethylhydrazino, represents in each case optionally        fluorine- and/or chlorine-substituted ethenyl, propenyl,        butenyl, propenyloxy, butenyloxy, propenylthio, butenylthio,        propenylamino, butenylamino, ethinyl, propinyl, butinyl,        propinyloxy, butinyloxy, propinylamino or butinylamino,        represents in each case optionally cyano-, fluorine-, chlorine-        or methyl-substituted cyclopropyl, cyclobutyl, cyclopentyl,        cyclohexyl, cyclopropylmethyl, cyclobutylmethyl,        cyclopentylmethyl or cyclohexylmethyl, represents in each case        optionally nitro-, cyano-, fluorine-, chlorine-, bromine-,        methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-,        trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,        difluoromethoxy-, trifluoromethoxy-, methoxycarbonyl-,        ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted phenyl,        phenylamino, phenylmethyl or phenylethyl, or represents in each        case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-,        methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-,        difluoromethyl-, trifluoromethyl-, dichloromethyl-,        trichloromethyl-, chlorodifluoromethyl-, fluorodichloromethyl-,        methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-,        trifluoromethoxy-, methylthio-, ethylthio-, n- or i-propylthio-,        difluoromethylthio-, trifluoromethylthio-, methoxycarbonyl-,        ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted monocyclic        or bicyclic heterocyclyl or heterocyclylalkyl from the group        consisting of furyl, furylmethyl, thienyl, thienylmethyl,        pyrrolidinyl, oxopyrrolidinyl, pyrrolyl, pyrrolylmethyl,        pyrazolyl, pyrazolylmethyl, imidazolyl, imidazolylmethyl,        2-oxo-1,3-diazacyclopentyl, oxazolyl, isoxazolyl,        oxazolylmethyl, isoxazolidinyl, thiazolyl, thiazolylmethyl,        piperidinyl, oxopiperidinyl, 2-oxo-1,3-diazacyclohexyl,        morpholinyl, piperazinyl, pyridinyl, pyridinylmethyl,        pyrimidinyl, pyrimidinylmethyl.    -   X very particularly preferably represents hydrogen, nitro,        cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or        i-propyl, difluoromethyl, trifluoromethyl, dichloromethyl,        trichloromethyl, methoxymethyl, methylthiomethyl,        methylsulphinylmethyl, methylsulphonylmethyl, methoxy, ethoxy,        difluoromethoxy, trifluoromethoxy, methylthio, ethylthio,        methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl        or dimethylaminosulphonyl.    -   Y very particularly preferably represents hydrogen, nitro,        cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl,        difluoromethyl, trifluoromethyl, dichloromethyl,        trichloromethyl, methoxymethyl, methylthiomethyl,        methylsulphinylmethyl, methylsulphonylmethyl, methoxy, ethoxy,        difluoromethoxy, trifluoromethoxy, methylthio, ethylthio,        methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl        or dimethylaminosulphonyl.    -   m very particularly preferably represents the number 0 or 1.    -   R³ very particularly preferably represents hydrogen, represents        in each case optionally fluorine- and/or chlorine-substituted        methyl, ethyl, n- or i-propyl, methylthio, ethylthio, n- or        i-propylthio, or represents phenyl, or—if m represents        2—optionally also together with a second radical R³ represents        oxygen, propane-1,3-diyl or butane-1,4-diyl.    -   R⁴ very particularly preferably represents hydroxyl, represents        formyloxy, represents in each case optionally fluorine- and/or        chlorine-substituted methoxy, ethoxy, n- or i-propoxy,        methylthio, ethylthio, n- or i-propylthio, methylsulphinyl,        ethylsulphinyl, methylsulphonyl, ethylsulphonyl, acetyloxy,        propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy,        ethoxycarbonyloxy, n- or i-propoxycarbonyloxy,        methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or        i-propylaminocarbonyloxy, methylsulphonyloxy, ethylsulphonyloxy,        n- or i-propylsulphonyloxy, represents in each case optionally        fluorine- and/or chlorine-substituted propenyloxy, butenyloxy,        propinyloxy or butinyloxy, represents in each case optionally        nitro-, cyano-, fluorine-, chlorine-, bromine- methyl-, ethyl-,        n- or i-propyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or        i-propoxy-, difluoromethoxy- or trifluoromethoxy-substituted        phenyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl,        phenylcarbonyloxy, phenylcarbonylmethoxy, phenylsulphonyloxy,        phenylmethoxy, phenylmethylthio, phenylmethylsulphinyl or        phenylmethylsulphonyl.    -   R⁵ very particularly preferably represents hydrogen, cyano,        fluorine, chlorine, represents in each case optionally fluorine-        and/or chlorine-substituted methyl, ethyl, n- or i-propyl,        methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or        i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl,        ethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, n- or        i-propoxycarbonyl, or represents in each case optionally cyano-,        fluorine-, chlorine- or methyl-substituted cyclopropyl.    -   R⁶ very particularly preferably represents hydrogen, represents        in each case optionally cyano-, fluorine-, chlorine-, methoxy or        ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or        t-butyl, represents in each case optionally fluorine- or        chlorine-substituted propenyl, butenyl, propinyl or butinyl,        represents in each case optionally fluorine-, chlorine- or        methyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or        cyclohexyl, or represents in each case optionally fluorine-,        chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-,        trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,        difluoromethoxy- or trifluoromethoxy-substituted phenyl or        phenylmethyl.    -   R⁷ very particularly preferably represents hydroxyl, represents        formyloxy, represents in each case optionally cyano-, fluorine-,        chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted        methoxy, ethoxy, n- or i-propoxy, acetyloxy, propionyloxy, n- or        i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or        i-propoxycarbonyloxy, methylaminocarbonyloxy,        ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy,        methylsulphonyloxy, ethylsulphonyloxy, n- or        i-propylsulphonyloxy, represents in each case optionally        fluorine- and/or chlorine-substituted propenyloxy, butenyloxy,        propinyloxy or butinyloxy, or represents in each case optionally        nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-,        n- or i-propyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or        i-propoxy, difluoromethoxy- or trifluoromethoxy-substituted        phenylmethoxy, phenylcarbonyloxy, phenylcarbonylmethoxy or        phenylsulphonyloxy.    -   R⁸ very particularly preferably represents hydrogen, cyano,        fluorine, chlorine, bromine, or represents in each case        optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted        methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- or        i-butyroyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl,        ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio,        n- or i-propylthio, methylsulphinyl, ethylsulphinyl,        methylsulphonyl or ethylsulphonyl.    -   R⁹ very particularly preferably represents hydrogen, represents        in each case optionally fluorine-, chlorine-, methoxy- or        ethoxy-substituted methyl, ethyl, n- or i-propyl, or represents        optionally fluorine-, chlorine- or methyl-substituted        cyclopropyl.    -   R¹⁰ very particularly preferably represents hydrogen, represents        in each case optionally fluorine-, chlorine-, methoxy- or        ethoxy-substituted methyl, ethyl, n- or i-propyl, or represents        optionally fluorine-, chlorine- or methyl-substituted        cyclopropyl.    -   R¹¹ very particularly preferably represents hydrogen, cyano,        fluorine, chlorine, bromine, or represents in each case        optionally fluorine-, chlorine-, methoxy-, or ethoxy-substituted        methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy,        methoxycarbonyl, ethoxy-carbonyl, n- or i-propoxycarbonyl,        methylthio, ethylthio, n- or i-propylthio, methylsulphinyl,        ethylsulphinyl, methylsulphonyl or ethylsulphonyl.    -   R¹ most preferably represents hydrogen, or represents in each        case optionally fluorine-, chlorine-, methoxy- or        ethoxy-substituted methyl, ethyl, n- or i-propyl, represents        methoxy or ethoxy or represents the grouping —C(Q)-R².    -   R² most preferably represents hydrogen, amino, hydrazino, or        represents in each case optionally fluorine-, chlorine-,        methoxy- or ethoxy-substituted methyl, ethyl or n- or i-propyl,        represents methylamino, ethylamino, n- or i-propylamino or        dimethylamino, represents in each case optionally fluorine-,        chlorine- or methyl-substituted cyclopropyl, cyclobutyl,        cyclopentyl or cyclohexyl, represents in each case optionally        nitro-, cyano-, fluorine-, chlorine-, bromine- methyl-, ethyl-        or n- or i-propyl-, methoxy-, ethoxy-, n- or        i-propoxy-substituted phenyl, phenylamino, phenylmethyl or        phenylethyl, or represents in each case optionally nitro-,        cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl,        difluoromethyl-, trifluoromethyl-, dichloromethyl-,        trichloromethyl-, chlorodifluoromethyl-, fluorodichloromethyl-,        methoxy-, ethoxy-, methylthio-, ethylthio-, difluoromethylthio-,        trifluoromethylthio-, methoxycarbonyl- or        ethoxycarbonyl-substituted furyl, furylmethyl, thienyl,        thienylmethyl, pyrrolyl or pyrrolylmethyl.    -   X most preferably represents hydrogen, nitro, fluorine,        chlorine, bromine, methyl, ethyl or trifluoromethyl.    -   Y most preferably represents hydrogen, nitro, cyano, fluorine,        chlorine, bromine, iodine, methyl, ethyl, difluoromethyl,        trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl,        methylthiomethyl, methylsulphinylmethyl, methylsulphonylmethyl,        methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio,        ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl,        ethylsulphonyl or dimethylaminosulphonyl.    -   R³ most preferably represents hydrogen or in each case        optionally fluorine- and/or chlorine-substituted methyl or        ethyl.    -   R⁴ most preferably represents hydroxyl.    -   R⁵ most preferably represents hydrogen, fluorine, chlorine or        represents in each case optionally fluorine- and/or        chlorine-substituted methyl, ethyl, methoxy or ethoxy.    -   R⁶ most preferably represents hydrogen or represents in each        case optionally fluorine-, chlorine-, methoxy- or        ethoxy-substituted methyl, ethyl, n- or i-propyl or n-, i-, s-        or t-butyl.    -   R⁷ most preferably represents hydroxyl, or represents in each        case optionally fluorine-, or chlorine-substituted methoxy or        ethoxy, or represents optionally nitro-, cyano-, fluorine-,        chlorine-, bromine, methyl-, ethyl-, trifluoromethyl-, methoxy-        or ethoxy-substituted phenylmethoxy.

Preference according to the invention is given to the compounds of theformula (I) which contain a combination of the meanings given above asbeing preferred.

Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningsgiven above as being particularly preferred.

Very particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningsgiven above as being very particularly preferred.

Most preference according to the invention is given to the compounds ofthe formula (I) which contain a combination of the meanings given aboveas being most preferred.

Particular emphasis is given to the compounds of the formulae (I-1) to(I-3):

Here, the A¹, A², Q, R¹, R², X, Y and Z each have the meanings givenabove as being preferred or being very particularly preferred.

Particular emphasis is furthermore given to the compounds of the generalformulae (I-2A) to (I-2D):

Here, m, A¹, A², Q, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, X andY each have the meanings given above as being preferred or as being veryparticularly preferred.

Among the compounds of the formulae (I-1) to (I-3) and (I-2A) to (I-2D),very particular emphasis is given to those in which A¹ represents asingle bond and A² represents methylene.

Among the compounds of the formulae (I-1) to (I-3) and (I-2A) to (I-2D),very particular emphasis is furthermore also given to those in which A¹represents O (oxygen) and A² represents ethane-1,2-diyl (dimethylene).

The general or preferred radical definitions given above apply both tothe end products of the formula (I) and, correspondingly, to thestarting materials or intermediates required in each case for thepreparation. These radical definitions can be combined with one anotheras desired, i.e. including combinations between the given preferredranges.

The novel substituted aryl ketones of the formula (I) have strong andselective herbicidal activity.

The novel substituted aryl ketones of the formula (I) are obtained when

-   -   (a) amino compounds of the general formula (II)

-   -   in which    -   A¹, A², R¹, X, Y and Z are as defined above.    -   are reacted with compounds of the general formula (III)

-   -   in which    -   Q and R² are as defined above and    -   Q¹ represents halogen, alkoxy, alkylthio, aryloxy or arylthio,        preferably represents chlorine, bromine, methoxy, ethoxy,        methylthio, ethylthio, phenyloxy or phenylthio,    -   —or, if appropriate, with corresponding iso(thio)cyanates—    -   if appropriate in the presence of one or more reaction        auxiliaries and if appropriate in the presence of one or more        diluents,    -   or when    -   (b) carboxylic acids of the general formula (IV)

-   -   in which    -   A¹, A², Q, R¹, R², X and Y are as defined above,    -   —or reactive derivatives thereof, such as, for example,        corresponding acid halides, acid cyanides or esters—    -   are reacted with compounds of the general formula (V)        H-Z   (V)    -   in which    -   Z is as defined above,    -   if appropriate in the presence of a dehydrating agent and also,        if appropriate in the presence of one or more reaction        auxiliaries and, if appropriate, in the presence of one or more        diluents,    -   or when    -   (c) substituted benzoyl ketones of the general formula (Ia)

-   -   in which    -   A¹, A², Q, R¹, R², R¹⁰, X and Y are as defined above,    -   are reacted with an orthoformic ester or with a        N,N-dimethyl-formamide acetal or with a cyanoformic ester or        with carbon disulphide and an alkylating agent and subsequently        with hydroxylamine or an acid adduct thereof,    -   if appropriate in the presence of one or more reaction        auxiliaries and if appropriate in the presence of one or more        diluents,    -   or when    -   (d) aryl ketones of the general formula (VI)

-   -   in which    -   A¹, A², Q, R¹, X, Y and Z are as defined above and    -   Q² represents halogen, alkoxy, alkylthio, aryloxy or arylthio,        preferably represents chlorine, bromine, methoxy, ethoxy,        methylthio, ethylthio, phenyloxy or phenylthio,    -   —or, if appropriate, corresponding iso(thio)cyanates—    -   are reacted with compounds of the general formula (VII)        H—R²   (VII)    -   in which    -   R² is as defined above,    -   if appropriate in the presence of one or more reaction        auxiliaries and if appropriate in the presence of one or more        diluents,    -   and following the practice of the process (a), (b), (c) or (d)        according to the invention, the resulting compounds of the        general formula (I) are, if appropriate and within the bounds of        the definition of substituents, subjected to subsequent        reactions (for example, substition, oxidation or reduction        reactions) according to customary methods for conversion into        other compounds of the general formula (I).

Using, for example,[3-(2-amino-ethoxy)-2-chloro-4-methylthio-phenyl]-(5-ethyl-4-isoxazolyl)-isoxazolyl)-methanoneand propionyl chloride as starting materials, the course of the reactionin the process (a) according to the invention can be illustrated by thefollowing equation:

Using, for example,4-bromo-3-[[(1-pyrrolidinylthioxomethyl)-amino]-methyl]-benzoic acid andcyclohexane-1,3-dione as starting materials, the course of the reactionin the process (b) according to the invention can be illustrated by thefollowing equation:

Using, for example,N-[2-chloro-5-(3-cyclopropyl-3-oxo-propanoyl)-benzyl]-acetamide,N,N-dimethyl-formamide diethyl acetal and hydroxylamine as startingmaterials, the course of the reaction in the process (c) according tothe invention can be illustrated by the following equation:

Using, for example, O-methylN-[[2-bromo-5-[(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-carbonyl]-phenyl]-methyl]-carbamateand pyrrolidine as starting materials, the course of the reaction of theprocess (d) according to the invention can be illustrated by thefollowing equation:

The formula (II) provides a general definition of the amino compounds tobe used as starting materials in the process (a) according to theinvention for preparing compounds of the general formula (I). In thegeneral formula (II), A¹, A², R¹, X, Y and Z preferably have thosemeanings which have already been mentioned above, in connection with thedescription of the compounds of the general formula (I) according to theinvention, as being preferred, particularly preferred, very particularlypreferred or most preferred for A¹, A², R¹, X, Y and Z.

The starting materials of the general formula (II) have hitherto notbeen disclosed in the literature; as novel substances, they also formpart of the subject-matter of the present application.

The novel amino compounds of the general formula (II) are obtained whenhalogen compounds of the general formula (VIII)

in which

-   A¹, A², X, Y and Z are as defined above and-   X¹ represents halogen (preferably fluorine, chlorine, bromine or    iodine, in particular chlorine or bromine),    are reacted with ammonia or amino compounds of the general formula    (IX)

in which

-   R¹ is as defined above,    if appropriate in the presence of a diluent, such as, for example,    tetrahydrofuran, and if appropriate under elevated pressure, at    temperatures between 0° C. and 100° C. (cf. the Preparation    Examples).

The intermediates of the general formula (VIII) are known and/or can beprepared by processes known per se (cf. WO-A-95/3 1446, WO-A-00/68227,Preparation Examples).

The intermediates of the general formula (IX) are known chemicals forsynthesis.

The formula (III) provides a general definition of the (thi)oxocompounds further to be used as starting materials in the process (a)according to the invention for preparing compounds of the generalformula (I). In the general formula (III), Q and R³ preferably havethose meanings which have already been given above, in connection withthe description of the compounds of the general formula (I) according tothe invention, as being preferred, particularly preferred, veryparticularly preferred or most preferred for Q and R³; Q¹ preferablyrepresents fluorine, chlorine, bromine, C₁–C₄-alkoxy, C₁–C₄-alkylthio,phenoxy or phenylthio, in particular chlorine, methoxy, ethoxy orphenoxy.

The starting materials of the general formula (III) are known organicchemicals for synthesis.

The formula (IV) provides a general definition of the carboxylic acidsto be used as starting materials in the process (b) according to theinvention for preparing compounds of the general formula (I). In thegeneral formula (IV), A¹, A², Q, R¹, R², X and Y preferably have thosemeanings which have already been given above, in connection with thedescription of the compounds of the general formula (I) according to theinvention, as being preferred, particularly preferred, very particularlypreferred or most preferred for A¹, A², Q, R¹, R², X and Y.

The starting materials of the general formula (IV) have hitherto notbeen disclosed in the literature; as novel substances, they also formpart of the subject-matter of the present application.

The novel carboxylic acids of the general formula (IV) are obtained when

(α) iso(thio)cyanates of the general formula (X)

-   -   in which    -   A¹, A², Q, X and Y are as defined above and    -   R represents hydrogen, an alkali metal or an alkaline earth        metal equivalent (preferably sodium or potassium) or alkyl        (preferably C₁–C₄-alkyl, in particular methyl or ethyl),    -   are reacted with compounds of the general formula (VII)        H—R²   (VII)    -   in which    -   R² is as defined above,    -   if appropriate in the presence of a diluent, such as, for        example, acetonitrile or ethanol, at temperatures between 0° C.        and 100° C., followed, if appropriate, by an ester hydrolysis        using customary methods (cf. the Preparation Examples),    -   or when

(β) amino compounds of the general formula (XI)

-   -   in which    -   A¹, A², R¹, X and Y are as defined above and    -   R represents hydrogen, an alkali metal or an alkaline earth        metal equivalent (preferably sodium or potassium) or alkyl        (preferably C₁–C₄-alkyl, in particular methyl or ethyl),    -   are reacted with (thi)oxo compounds of the general formula (III)

-   -   in which    -   Q and R² are as defined above and    -   Q¹ represents halogen, alkoxy, alkylthio, aryloxy or arylthio,        preferably chlorine, bromine, methoxy, ethoxy, methylthio,        ethylthio, phenyloxy or phenylthio,    -   —or, if appropriate, with corresponding iso(thio)cyanates—    -   if appropriate in the presence of one or more reaction        auxiliaries, such as, for example, potassium carbonate or        triethylamine, and if appropriate in the presence of one or more        diluents, such as, for example, acetonitrile or        N,N-dimethyl-formamide, at temperatures between 0° C. and 100°        C.

The formula (V) provides a general definition of the compounds furtherto be used as starting materials in the process (b) according to theinvention for preparing compounds of the general formula (I). In thegeneral formula (V), Z preferably has that meaning which has alreadybeen given above, in connection with the description of the compounds ofthe general formula (I) according to the invention, as being preferred,particularly preferred, very particularly preferred or most preferredfor Z.

The starting materials of the general formula (V) are known organicchemicals for synthesis.

The formula (Ia) provides a general definition of the substitutedbenzoyl ketones to be used as starting materials in the process (c)according to the invention for preparing compounds of the generalformula (I). In the general formula (Ia), A¹, A², Q, R¹, R², R¹⁰, X andY preferably have those meanings which have already been mentionedabove, in connection with the description of the compounds of thegeneral formula (I) according to the invention, as being preferred,particularly preferred, very particularly preferred or most preferredfor A¹, A², Q, R¹, R², R¹⁰, X and Y.

As novel substances, the starting materials of the general formula (Ia)also form part of the subject-matter of the present application; theycan be prepared by the process (a) or (b) according to the invention.

The formula (VI) provides a general definition of the aryl ketones to beused as starting materials in the process (d) according to the inventionfor preparing compounds of the general formula (I). In the generalformula (VI), A¹, A², Q, R¹, X, Y and Z preferably have those meaningswhich have already been mentioned above, in connection with thedescription of the compounds of the general formula (I) according to theinvention, as being preferred, particularly preferred, very particularlypreferred or most preferred for A¹, A², Q, R¹, X, Y and Z; Q² preferablyrepresents fluorine, chlorine, bromine, C₁–C₃-alkoxy, C₁–C₃-alkylthio,phenoxy or phenylthio, in particular chlorine, methoxy, ethoxy orphenoxy.

The starting materials of the formula (VI) can be prepared by processesknown to the person skilled in the art.

The formula (VII) provides a general definition of the compounds furtherto be used as starting materials in the process (d) according to theinvention for preparing compounds of the general formula (I). In thegeneral formula (VII), R² preferably has that meaning which has alreadybeen mentioned above, in connection with the description of the generalformula (I), as being preferred, particularly preferred, veryparticularly preferred or most preferred for R².

The starting materials of the general formula (VII) are known organiccompounds.

The formula (X) provides a general definition of the iso(thio)cyanatesto be used as starting materials in the process (cc) according to theinvention for preparing compounds of the general formula (IV). In thegeneral formula (X), A¹, A², Q, X and Y preferably have that meaningwhich has already been mentioned above, in connection with thedescription of the general formula (I), as being preferred, particularlypreferred, very particularly preferred or most preferred for A¹, A², Q,X and Y.

The starting materials of the general formula (X) can be obtained byprocesses known to the person skilled in the art.

The formula (XI) provides a general definition of the amino compounds tobe used as starting materials in the process (p) according to theinvention for preparing compounds of the general formula (IV). In thegeneral formula (XI), A¹, A², R¹, X and Y preferably have that meaningwhich has already been mentioned above, in connection with thedescription of the general formula (I), as being preferred, particularlypreferred, very particularly preferred or most preferred for A¹, A², R¹,X and Y.

The starting materials of the general formula (XI) can be prepared byprocesses known to the person skilled in the art.

The process (a), (b), (c) and (d) according to the invention arepreferably carried out using one or more reaction auxiliaries. Suitablereaction auxiliaries for the processes (a), (b), (c) and (d) accordingto the invention are, in general, the customary inorganic or organicbases or acid acceptors. These preferably include alkali metal oralkaline earth metal acetates, amides, carbonates, bicarbonates,hydrides, hydroxides or alkoxides, such as, for example, sodium acetate,potassium acetate, or calcium acetate, lithium amide, sodium amide,potassium amide or calcium amide, sodium carbonate, potassium carbonateor calcium carbonate, sodium bicarbonate, potassium bicarbonate orcalcium bicarbonate, lithium hydride, sodium hydride, potassium hydrideor calcium hydride, lithium hydroxide, sodium hydroxide, potassiumhydroxide or calcium hydroxide, sodium methoxide, ethoxide, n- ori-propoxide, n-, i-, s- or t-butoxide or potassium methoxide, ethoxide,n- or i-propoxide, n-, i-, s- or t-butoxide; furthermore also basicorganic nitrogen compounds, such as, for example, trimethylamine,triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine,N,N-dimethyl-cyclohexylamine, dicyclohexylamine,ethyl-dicyclohexylamine, N,N-dimethyl-aniline, N,N-dimethyl-benzylamine,pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-,3,4-dimethyl- and 3,5-dimethylpyridine, 5-ethyl-2-methyl-pyridine,4-dimethylamino-pyridine, N-methyl-piperidine, N-ethyl-piperidine,N-methyl-morpholine, N-ethyl-morpholine, 1,4-diaza-bicyclo[2.2.2]-octane(DABCO), 1,5-diazabicyclo[4.3.0]-non-5-ene (DBN), or1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU).

Further reaction auxiliaries suitable for the processes (a), (b), (c)and (d) according to the invention are phase-transfer catalysts.Examples of such catalysts which may be mentioned are:

Tetrabutylammonium bromide, tetrabutylammonium chloride,tetraoctylammonium chloride, tetrabutylammonium hydrogensulphate,methyl-trioctylammonium chloride, hexadecyl-trimethylammonium chloride,hexadecyl-triethylammonium bromide, benzyl-trimethylammonium chloride,benzyl-triethylammonium chloride, benzyl-trimethylammonium hydroxide,benzyl-triethylammonium hydroxide, benzyltributylammonium chloride,benzyl-tributylammonium bromide, tetrabutylphosphonium bromide,tetrabutylphosphonium chloride, tributyl-hexadecylphosphonium bromide,butyl-triphenylphosphonium chloride, ethyl-trioctylphosphonium bromide,tetra-phenylphosphonium bromide.

The process (b) according to the invention for preparing the novelsubstituted aryl ketones of the general formula (I) is, if appropriate,carried out using a dehydrating agent. Here, suitable dehydrating agentsare the chemicals customarily suitable for binding water.

Examples which may be mentioned are dicyclohexylcarbodiimide,carbonyl-bisimidazole and propanephosphonic anhydride.

Dehydrating agents which may be mentioned as being particularly suitableare dicyclohexcylcarbodimide and propanephosphonic anhydride.

The processes according to the invention for preparing the compounds ofthe general formula (I) are preferably carried out using diluents.Suitable diluents for carrying out the processes (a), (b), (c) and (d)according to the invention are, in addition to water, especially inertorganic solvents. These include, in particular, aliphatic, alicyclic oraromatic, optionally halogenated hydrocarbons, such as, for example,benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene,petroleum ether, hexane, cyclohexane, dichloromethane, chloroform,carbon tetrachloride; ethers, such as diethyl ether, diisopropyl ether,dioxane, tetrahydrofuran or ethylene glycol dimethyl ether or ethyleneglycol diethyl ether, ketones, such as acetone, butanone or methylisobutyl ketone; nitriles, such as acetonitrile, propionitrile orbutyronitrile; amides, such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone orhexamethylphosphoric triamide; esters, such as methyl acetate or ethylacetate; sulphoxides, such as dimethyl sufoxide; alcohols, such asmethanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether,ethylene glycol monoethyl ether, diethylene glycol monomethyl ether,diethylene-glycol monoethyl ether, mixtures thereof with water or purewater.

When carrying out the processes (a), (b), (c) and (d) according to theinvention, the reaction temperatures can be varied within a relativelywide range. In general, the processes are carried out at temperaturesbetween 0° C. and 150° C., preferably between 10° C. and 120° C.

The process according to the invention is generally carried out underatmospheric pressure. However, it is also possible to carry out theprocesses according to the invention under elevated or reducedpressure—in general between 0.1 bar and 10 bar.

For carrying out the processes according to the invention, the startingmaterials are generally employed in approximately equimolar amounts.However, it is also possible to use a relatively large excess of one ofthe components. The reaction is generally carried out in a suitablediluent in the presence of a reaction auxiliary, and the reactionmixture is generally stirred at the required temperature for severalhours. Work-up is carried out by customary methods (cf. the PreparationExamples).

The active compounds according to the invention can be used asdefoliants, desiccants, haulm killers and, especially, as weed killers.Weeds in the broadest sense are understood to mean all plants which growin locations where they are undesired. Whether the substances accordingto the invention act as total or selective herbicides dependsessentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus,Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium,Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus,Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha,Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum,Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola,Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis,Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca,Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis,Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina,Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis,Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera,Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum,Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria,Sorghum.

Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena,Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

The active compounds according to the invention are suitable, dependingon the concentration, for the total control of weeds, for example onindustrial terrain and rail tracks, and on paths and areas with andwithout tree plantings. Similarly, the active compounds according to theinvention can be employed for controlling weeds in perennial crops, forexample forests, decorative tree plantings, orchards, vineyards, citrusgroves, nut orchards, banana plantations, coffee plantations, teaplantations, rubber plantations, oil palm plantations, cocoaplantations, soft fruit plantings and hop fields, on lawns, turf andpastureland, and for the selective control of weeds in annual crops.

The compounds of the formula (I) according to the invention have strongherbicidal activity and a broad active spectrum when used on the soiland on above-ground parts of plants. To a certain extent they are alsosuitable for the selective control of monocotyledonous anddicotyledonous weeds in monocotyledonous and dicotyledonous crops, bothby the pre-emergence and by the post-emergence method.

At certain concentrations or application rates, the active compoundsaccording to the invention can also be employed for controlling animalpests and fungal or bacterial plant diseases. If appropriate, they canalso be used as intermediates or precursors for the synthesis of otheractive compounds.

All plants and plant parts can be treated in accordance with theinvention. Plants are to be understood as meaning in the present contextall plants and plant populations such as desired and undesired wildplants or crop plants (including naturally occurring crop plants). Cropplants can be plants which can be obtained by conventional plantbreeding and optimization methods or by biotechnological and recombinantmethods or by combinations of these methods, including the transgenicplants and inclusive of the plant cultivars protectable or notprotectable by plant breeders' rights. Plant parts are to be understoodas meaning all parts and organs of plants above and below the ground,such as shoot, leaf, flower and root, examples which may be mentionedbeing leaves, needles, stalks, stems, flowers, fruit bodies, fruits,seeds, roots, tubers and rhizomes. The plant parts also includeharvested material, and vegetative and generative propagation material,for example cuttings, tubers, rhizomes, offsets and seeds.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plants(weeds, harmful plants) and/or plant species and plant cultivars (cropplants) obtained by conventional biological breeding methods, such ascrossing or protoplast fusion, and parts thereof, are treated. In afurther preferred embodiment, transgenic plants and plant cultivarsobtained by genetic engineering, if appropriate in combination withconventional methods (Genetically Modified Organisms), and parts thereofare treated. The term “parts” or “parts of plants” or “plant parts” hasbeen explained above.

Plant cultivars are to be understood as meaning crop plants havingcertain properties (“traits”) which have been obtained by conventionalbreeding, by mutagenesis or by recombinant DNA techniques. They can becultivars, bio- or genotypes.

The transgenic plants or plant cultivars (i.e. those obtained by geneticengineering) which are treated according to the invention include allplants which, in the genetic modification, received genetic materialwhich imparted particularly advantageous useful properties (“traits”) tothese plants. Examples of such properties are better plant growth,increased tolerance to high or low temperatures, increased tolerance todrought or to water or soil salt content, increased floweringperformance, easier harvesting, accelerated maturation, higher harvestyields, better quality and/or a higher nutritional value of theharvested products, better storage stability and/or processability ofthe harvested products. Further and particularly emphasized examples ofsuch properties are a better defence of the plants against animal andmicrobial pests, such as against insects, mites, phytopathogenic fungi,bacteria and/or viruses, and also increased tolerance of the plants tocertain herbicidally active compounds. Examples of transgenic plantswhich may be mentioned are the important crop plants, such as cereals(including rice), maize, soya beans, potatoes, cotton, beets, cultivatedgrasses such as golfing greens and ornamental lawns, oilseed rape, fruitplants (with the fruits apples, pears, citrus fruits and grapes), andplantation crops, such as oil and rubber trees, where particularemphasis is given to cereals including rice), maize, soya beans,potatoes, cotton, beets and oilseed rape. Traits that are emphasized arein particular increased defence of the plants against insects by toxinsformed in the plants, in particular those formed in the plants by thegenetic material from Bacillus thuringiensis (for example by the genesCryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIA, CryIIIB2, Cry9c Cry2Ab,Cry3Bb and CryIF and also combinations thereof) (hereinbelow referred toas “Bt plants”). Traits that are also particularly emphasized are theincreased defence of the plants to fungi, bacteria and viruses bysystemic acquired resistance (SAR), systemin, phytoalexins, elicitorsand resistance genes and correspondingly expressed proteins and toxins.Traits that are furthermore particularly emphasized are the increasedtolerance of the plants to certain herbicidally active compounds andclasses of active compounds, such as glyphosate orglufosinate/phosphinotricin (for example the “PAT” gene), ALSinhibitors, such as imidazolinones, sulphonylureas and others, PPOinhibitors (for example plants having Acuron genes), 4-HPD inhibitors,such as isozazoles (for example isoxaflutole), ACCase inhibitors, suchas sethoxydim, and also bromoxynil.

The genes which impart the desired traits in question can also bepresent in combinations with one another in the transgenic plants.Examples of “Bt plants” which may be mentioned are maize cultivars,cotton cultivars, soya bean cultivars and potato cultivars which aresold under the trade names YIELD GARD® (for example maize, cotton, soyabeans), KnockOut® (for example maize), StarLink® (for example maize),Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples ofherbicide-tolerant plants which may be mentioned are maize cultivars,cotton cultivars, soya bean cultivars, cereal cultivars including ricecultivars, beet cultivars and oilseed rape cultivars which are soldunder the trade names Roundup Ready® (tolerance to glyphosate, forexample maize, cotton, soya bean, beets, oilseed rape), Liberty Link®(tolerance to glufosinate, for example oilseed rape, maize, beets), IMI®(tolerance to imidazolinones) and STS® (tolerance to sulphonylureas, forexample maize). Herbicide-resistant plants (plants bred in aconventional manner for herbicide tolerance) which may be mentionedinclude the cultivars sold under the name Clearfield® (for examplemaize, rice).

Of course, these statements also apply to plant cultivars having thesegenetic traits or genetic traits still to be developed, which plantswill be developed and/or marketed in the future.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions to be used according to theinvention—also in combination with other agrochemical active compounds—,better plant growth, increased tolerance to high or low temperatures,increased tolerance to drought or to water or soil salt content,increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, better quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products are possible whichexceed the effects which were actually to be expected.

The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the generalformula (I) or the active compound mixtures according to the inventionwhere in addition to the good control of weed plants, the abovementionedsynergistic effects with the transgenic plants or plant cultivars occur.The preferred ranges stated above for the active compounds or mixturesalso apply to the treatment of these plants. Particular emphasis isgiven to the treatment of plants with the compounds or mixturesspecifically mentioned in the present text.

The treatment according to the invention of the plants and plant partswith the active compounds is carried out directly or by allowing thecompounds to act on their surroundings, environment or storage space bythe customary treatment methods, for example by immersion, spraying,evaporation, fogging, scattering, painting on and, in the case ofpropagation material, in particular in the case of seeds, also byapplying one or more coats.

The active compounds can be converted into the customary formulationssuch as solutions, emulsions, wettable powders, suspensions, powders,dusts, pastes, soluble powders, granules, suspension-emulsionconcentrates, natural and synthetic materials impregnated with activecompound, and microencapsulations in polymeric materials.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents and/orsolid carriers, optionally with the use of surfactants, that is,emulsifiers and/or dispersants, and/or foam formers.

If the extender used is water, it is also possible, for example, to useorganic solvents as cosolvents. The following are essentially suitableas liquid solvents: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample mineral oil fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethylformamide and dimethylsulphoxide, or else water.

Suitable solid carriers are: for example ammonium salts and groundnatural minerals such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals such as highly-disperse silica, alumina and silicates; suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks such as calcite, marble, pumice, sepiolite and dolomite,or else synthetic granules of inorganic and organic minerals, andgranules of organic material such as sawdust, coconut shells, maize cobsand tobacco stalks; suitable emulsifiers and/or foam formers are: forexample nonionic and anionic emulsifiers such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates,or else protein hydrolysates; suitable dispersants are: for examplelignin-sulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic colorants suchalizarin colorants, azo colorants and metal phthalocyanine colorants,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

For controlling weeds, the active compounds according to the invention,as such or in their formulations, can also be used as mixtures withknown herbicides and/or substances which improve the compatibility withcrop plants (“safeners”), finished formulations or tank mixes beingpossible. Also possible are mixtures with weed-killers comprising one ormore known herbicides and a safener.

Suitable components for the mixtures are known herbicides, for exampleacetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne, amicarbazone, amidochlor, amidosulfuron, amitrole,anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid,benazolin (-ethyl), benfuresate, bensulfuiron (-methyl), bentazon,benzfendizone, benzobicyclon, benzofenap, benzoylprop (-ethyl),bialaphos, bifenox, bispyribac (-sodium), bromacil, bromobutide,bromofenoxim, bromoxynil, butachlor, butafenacil (-allyl), butenachlor,butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone(-ethyl), chlomethoxyfen, chloramben, chloridazon, chlorimuron (-ethyl),chlornitrofen, chlorsulfuron, chlorthiamid, chlortoluron, cinidon(-ethyl), cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop(-propargyl), clomazone, clomeprop, clopyralid, cloransulam (-methyl),cumyluron, cyanazine, cybutryne, cycloate, cyclosulfamuron, cycloxydim,cyhalofop (-butyl), 2,4-D, 2,4-DB, desmedipham, diallate, dicamba,dichlobenil, dichlorprop (—P), diclofop (-methyl), diclosulam, diethatyl(-ethyl), difenopenten (-ethyl), difenzoquat, diflufenican,diflufenzopyr, dikegulac (-sodium), dimefuron, dimepiperate,dimethachlor, dimethametryn, dimethenamid, dimexyflam, dinitramine,diphenamid, diquat (-dibromide), dithiopyr, diuron, dymron, epropodan,EPTC, esprocarb, ethalfluralin, ethametsulfuron (-methyl), ethiozin,ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop(—P-ethyl), fentrazamide, flamprop (-M-isopropyl, -M-methyl),flazasulfuron, florasulam, fluazifop (—P-butyl), fluazolate,flucarbazone (-sodium), fluchloralin, flufenacet, flumetsulam,flumiclorac (-pentyl), flumioxazin, flumipropyn, fluometuron,fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil,flurpyrsulfuron (-methyl, -sodium), flurenol (-butyl), fluridone,fluroxypyr (-butoxypropyl, -meptyl), flurprimidol, flurtamone,fluthiacet (-methyl), fomesafen, foramsulfuron, glufosinate (-ammonium),glyphosate (-ammonium, -isopropylammonium), halosafen, halosulfuron(-methyl), haloxyfop (-ethoxyethyl, —P-methyl), hexazinone,imazamethabenz (-methyl), imazamethapyr, imazamox, imazapic, imazapyr,imazaquin, imazethapyr, imazosulfuron, iodosulfuron (-methyl, -sodium),ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole,isoxadifen (-ethyl), isoxaflutole, isoxapyrifop, ketospiradox, lactofen,lenacil, linuron, MCPA, mecoprop (—P), mefenacet, mesotrione,metamitron, metazachlor, methabenzthiazuron, methyldymron, metobenzuron,metobromuron, (S—) metolachlor, metosulam, metoxuron, metribuzin,metsulfuron (-methyl), molinate, monolinuron, naproanilide, napropamide,neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl,oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat,pelargonic acid, pendimethalin, pendralin, pentoxazone, pethoxamid,phenmedipham, picolinafen, piperophos, pretilachlor, primisulfuron(-methyl), profluazol, profoxydim, prometryn, propachlor, propanil,propaquizafop, propisochlor, propoxycarbazone (-sodium), propyzamide,prosulfocarb, prosulfuron, pyraflufen (-ethyl), pyrazogyl, pyrazolate,pyrazosulfuron (-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb,pyridafol, pyridate, pyridatol, pyriftalid, pyriminobac (-methyl),pyrithiobac (-sodium), quinchlorac, quinmerac, quinoclamine, quizalofop(—P-ethyl, —P-tefuryl), rimsulfuron, sethoxydim, simazine, simetryn,sulcotrione, sulfentrazone, sulfometuron (-methyl), sulfosate,sulfosulfuron, tebutam, tebuthiuron, tepraloxydim, terbuthylazine,terbutryn, thenylchlor, thiazopyr, thidiazimin, thifensulfuron(-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate,triasulfuron, tribenuron (-methyl), triclopyr, tridiphane, trifluralin,trifloxysulfuron, triflusulfuron (-methyl), tritosulfuron.

Furthermore suitable for the mixtures are known safeners, for exampleAD-67, BAS-145138, benoxacor, cloquintocet (-mexyl), cyometrinil, 2,4-D,DKA-24, dichlormid, dymron, fenclorim, fenchlorazol (-ethyl), flurazole,fluxofenim, furilazole, isoxadifen (-ethyl), MCPA, mecoprop (—P),mefenpyr (-diethyl), MG-191, oxabetrinil, PPG-1292, R-29148.

A mixture with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, is also possible.

The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in a customary manner, for example bywatering, spraying, atomizing or broadcasting.

The active compounds according to the invention can be applied bothbefore and after emergence of the plants. They can also be incorporatedinto the soil before sowing.

The amount of active compound used can vary within a relatively widerange. It depends essentially on the nature of the desired effect. Ingeneral, the amounts used are between 1 g and 10 kg of active compoundper hectare of soil surface, preferably between 5 g and 5 kg per ha.

The preparation and the use of the active compounds according to theinvention is illustrated by the examples below.

PREPARATION EXAMPLES Example 1

(Process (a))

0.28 g (3.6 mmol) of acetyl chloride is added to a suspension of 1.0 g(2.9 mmol) of[3-(2-aminoethoxy)-2,4-dichloro-phenyl]-(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-methanoneand 0.8 g (5.8 mmol) of potassium carbonate in 6 ml of acetonitrile, andthe reaction mixture is stirred at room temperature (about 20° C.) for24 hours. The solvent is then removed under reduced pressure and theresidue is dissolved in a little water. The aqueous solution is washedwith dichloromethane and then acidified with conc. hydrochloric acid andextracted with ethyl acetate. The organic phase is washed with saturatedaqueous sodium chloride solution, dried over sodium sulphate andfiltered. From the filtrate, the solvent is carefully distilled offunder reduced pressure.

This gives 0.8 g (71.5% of theory) ofN-(2-{2,6-dichloro-3-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-carbonyl]-phenoxy}-ethyl)-acetamide(Example I-2-1) as an orange-yellow glass-like solid.

log P=1.41.

Example 2

(Process (a))

0.24 g (3.3 mmol) of methyl isothiocyanate is added to a suspension of0.5 g (1.45 mmol) of[3-(2-amino-ethoxy)-2,4-dichloro-phenyl]-(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-methanonein 10 ml of methanol, and the reaction mixture is heated at the boilunder reflux for 24 hours. Water and ethyl acetate are added and theorganic phase is then separated off, washed with saturated aqueoussodium chloride solution, dried over sodium sulphate and filtered. Fromthe filtrate, the solvent is carefully distilled off under reducedpressure.

This gives 0.55 g (91% of theory) ofN-(2-{2,6-dichloro-3-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-carbonyl]-phenoxy}-ethyl)-N′-methyl-thiourea(Example I-2-2) as an orange-yellow viscous oil.

log P=1.60.

Example 3

(Process (b))

0.7 g (6.25 mmol) of 1,3-cyclohexanedione and 2.0 g (6.25 mmol) ofN-(3-carboxyl-2,6-dichloro-benzyl)-N′-isopropyl-thiourea are initiallycharged to 50 ml of acetonitrile. 1.5 g (7.25 mmol) ofdicyclohexylcarbodiimide are added and the mixture is stirred at roomtemperature (about 20° C.) for 15 hours. 0.7 g (7 mmol) of triethylamineand 0.7 g (8 mmol) of 2-hydroxy-2-methyl-propionitrile is then added,and the mixture is stirred at room temperature for another 15 hours. Themixture is then stirred with 50 ml of aqueous 1M potassium carbonatesolution and filtered off with suction, and the filtrate is acidified topH 4 using hydrochloric acid. The mixture is extracted three times within each case 30 ml of dichloromethane and the combined organic phasesare dried with magnesium sulphate and filtered. The solvent is thenremoved under reduced pressure.

This gives 1.1 g (30% of theory) ofN-(3-(cyclohex-1-en-2-ol-6-on-1-ylcarbonyl)-2,4-dichlorobenzyl)-N′-isopropyl-thiourea(Example I-2-3) as an oily residue.

log P=2.74.

Example 4

(Subsequent Reaction)

0.25 g (1.0 mmol) of 1-bromo-4-(bromomethyl)-benzene and 0.15 g of1,8-diazabicyclo-(5.4.0)-undec-7-en (DBU) are added to a solution of0.193 g (0.5 mmol) ofN-(2-{2,6-dichloro-3-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-carbonyl]-phenoxy}-ethyl)-acetamidein 6 ml of toluene, and the reaction mixture is heated at the boil underreflux for 9 hours. The supernatant toluene phase is decanted off andthe oily residue that remains is separated by column chromatographyusing the mobile phase dichloromethane/methanol (9:1).

This gives 0.12 g (43% of theory) ofN-{2-[3-({5-[(4-bromo-benzyl)-oxy]-1-ethyl-1H-pyrazol-4-yl}-carbonyl)-2,6-dichloro-phenoxy]-ethyl}-acetamide(Example I-2-4) as a yellow viscous oil.

log P=2.06.

Analogously to Examples 1 to 4 and in accordance with the generaldescription of the preparation processes according to the invention, itis also possible to prepare, for example, the compounds of the generalformula (I)—or of the formulae (I-1) to (I-3) or the formulae (I-2a) to(I-2d)—listed in Table 1 below.

TABLE 1 Examples of compounds of the formula (I-2) (I-2)

(position) (position) Physical Ex. No. A¹ A² Q R¹ R² X Y Z data I-2-5 O(CH₂)₂ O H

(2)Cl (4)Cl

log P = 1.64^(a)) I-2-6 O (CH₂)₂ O H

(2)Cl (4)Cl

log P = 1.78^(a)) I-2-7 O (CH₂)₂ O H

(2)Cl (4)Cl

log P = 2.63^(a)) I-2-8 O (CH₂)₂ O

(2)Cl (4)Cl

I-2-9 — CH₂ S H

(2)Cl (4)Cl

log P = 3.05^(a)) I-2-10 — CH₂ O C₃H₇-i

(2)Cl (4)Cl

log P = 2.86^(a)) I-2-11 — CH₂ O C₃H₇-i

(2)Cl (4)Cl

log P 2.02^(a)) I-2-12 — CH₂ O C₃H₇-i NH₂ (2)Cl (4)Cl

log P = 2.03^(a)) I-2-13 O (CH₂)₂ O H

(2)Cl (4)Cl

log P = 2.12^(a)) I-2-14 — CH₂ O C₃H₇-i NH₂ (2)Cl (4)Cl

log P = 1.32^(a)) I-2-15 — CH₂ O C₃H₇-i

(2)Cl (4)Cl

log P = 2.33^(a)) I-2-16 — CH₂ O C₃H₇-i

(2)Cl (4)Cl

log P = 1.42^(a)) I-2-17 — CH₂ O C₃H₇-i N(CH₃)₂ (2)Cl (4)Cl

log P = 2.82^(a)) I-2-18 — CH₂ O C₃H₇-i N(CH₃)₂ (2)Cl (4)Cl

log P = 2.00^(a)) I-2-19 — CH₂ O H

(2)Cl (4)Cl

log P = 1.95^(a)) I-2-20 — CH₂ O H

(2)Cl (4)Cl

I-2-21 — CH₂ O H N(CH₃)₂ (2)Cl (4)Cl

log P = 1.87^(a)) I-2-22 — CH₂ O H

(2)Cl (4)Cl

log P = 1.35^(a)) I-2-23 — CH₂ O H N(CH₃)₂ (2)Cl (4)Cl

log P = 1.13^(a)) I-2-24 — CH₂ O

N(CH₃)₂ (2)Cl (4)Cl

log P = 2.45^(a)) I-2-25 — CH₂ O

N(CH₃)₂ (2)Cl (4)Cl

log P = 1.69^(a)) I-2-26 — CH₂ O

(2)Cl (4)Cl

I-2-27 — CH₂ O

(2)Cl (4)Cl

I-2-28 — CH₂ O

(2)Cl (4)Cl

I-2-29 — CH₂ O

(2)Cl (4)Cl

I-2-30 — CH₂ O H

(2)Cl (4)Cl

I-2-31 — CH₂ O H

(2)Cl (4)Cl

I-2-32 — CH₂ O H

(2)Cl (4)Cl

I-2-33 — CH₂ O H

(2)Cl (4)Cl

I-2-34 — CH₂ O H

(2)Cl (4)Cl

I-2-35 — CH₂ O H

(2)Cl (4)Cl

I-2-36 — CH₂ O H

(2)Cl (4)Cl

I-2-37 — CH₂ O H

(2)Cl (4)Cl

I-2-38 — CH₂ O CH₃ NH₂ (2)Cl (4)Cl

I-2-39 — CH₂ O CH₃ NH₂ (2)Cl (4)Cl

I-2-40 — CH₂ O H NH₂ (2)Cl (4)Cl

I-2-41 — CH₂ O H NH₂ (2)Cl (4)Cl

I-2-42 — CH₂ O C₃H₇-i

(2)Cl (4)Cl

log P = 4.25^(a)) I-2-43 — CH₂ O C₃H₇-i

(2)Cl (4)Cl

log P = 3.19^(a)) I-2-44 — CH₂ O C₃H₇-i OC₂H₅ (2)Cl (4)Cl

log P = 3.69^(a)) I-2-45 — CH₂ O C₃H₇-i OC₂H₅ (2)Cl (4)Cl

log P = 2.69^(a)) I-2-46 — CH₂ O H OC₂H₅ (2)Cl (4)Cl

I-2-47 — CH₂ O H OC₂H₅ (2)Cl (4)Cl

I-2-48 — CH₂ O H OC₃H₇-i (2)Cl (4)Cl

I-2-49 — CH₂ O H OC₃H₇-i (2)Cl (4)Cl

I-2-50 — CH₂ O CH₃ OC₂H₅ (2)Cl (4)Cl

I-2-51 — CH₂ O CH₃ OC₂H₅ (2)Cl (4)Cl

I-2-52 — CH₂ O H NHOCH₃ (2)Cl (4)Cl

I-2-53 — CH₂ O H NHOCH₃ (2)Cl (4)Cl

I-2-54 — CH₂ O H N(CH₃)O—CH₃ (2)Cl (4)Cl

I-2-55 — CH₂ O H N(CH₃)O—CH₃ (2)Cl (4)Cl

I-2-56 — CH₂ O

(2)Cl (4)Cl

log P = 2.75^(a)) I-2-57 — CH₂ O

(2)Cl (4)Cl

I-2-58 — CH₂ S C₃H₇-i

(2)Cl (4)Cl

log P = 1.91^(a)) I-2-59 — CH₂ O CH₃

(2)Cl (4)Cl

log P = 1.81^(a)) I-2-60 — CH₂ O CH₃

(2)Cl (4)Cl

log P = 1.11^(a)) I-2-61 — CH₂ O CH₃ N(CH₃)₂ (2)Cl (4)Cl

log P = 2.26^(a)) I-2-62 — CH₂ O CH₃ N(CH₃)₂ (2)Cl (4)Cl

log P = 1.48^(a)) I-2-63 — CH₂ S CH₃

(2)Cl (4)SO₂CH₃

log P = 1.81^(a)) I-2-64 — CH₂ S CH₃

(2)Cl (4)SO₂CH₃

log P = 1.00^(a)) I-2-65 — CH₂ O H NH₂ (2)Cl (4)SO₂CH₃

log P = 0.30^(a)) I-2-66 — CH₂ O H

(2)Cl (4)SO₂CH₃

log P = 1.57^(a)) I-2-67 O (CH₂)₂ O H CH₃ (2)Cl (4)Cl

I-2-68 O (CH₂)₂ O H

(2)Cl (4)Cl

log P = 2.28^(a)) I-2-69 O (CH₂)₂ O H OC₃H₇-i (2)Cl (4)Cl

log P = 2.98^(a)) I-2-70 O (CH₂)₂ O H OC₃H₇-i (2)Cl (4)Cl

log P = 2.46^(a)) I-2-71 O (CH₂)₂ O H C₂H₅ (2)Cl (4)Cl

I-2-72 O (CH₂)₂ O H C₂H₅ (2)Cl (4)Cl

log P = 1.64^(a)) I-2-73 O (CH₂)₂ O H

(2)Cl (4)Cl

log P = 1.84^(a)) I-2-74 O (CH₂)₂ O H

(2)Cl (4)Cl

log P = 1.37^(a)) I-2-75 O (CH₂)₂ S H

(2)Cl (4)Cl

log P = 2.23^(a)) I-2-76 O (CH₂)₂ S H

(2)Cl (4)Cl

log P = 1.73^(a)) I-2-77 O (CH₂)₂ O H CF₃ (2)Cl (4)Cl

I-2-78 O (CH₂)₂ O H CF₃ (2)Cl (4)Cl

I-2-79 — CH₂ O H NH₂ (2)Cl (4)SO₂CH₃ log P = 1.23^(a)) I-2-80 — CH₂ O H

(2)Cl (4)SO₂CH₃

log P = 0.74^(a)) I-2-81 — CH₂ O H

(2)Cl (4)SO₂CH₃

log P = 1.58^(a)) I-2-82 — CH₂ O H N(CH₃)₂ (2)Cl (4)SO₂CH₃

log P = 1.58^(a)) I-2-83 — CH₂ O H N(CH₃)₂ (2)Cl (4)SO₂CH₃

log P = 0.77^(a)) I-2-84 — CH₂ O OCH₃

(2)Cl (4)Cl

I-2-85 — CH₂ O OCH₃

(2)Cl (4)Cl

I-2-86 — CH₂ O OCH₃

(2)Cl (4)SO₂CH₃

I-2-87 — CH₂ O OCH₃

(2)Cl (4)SO₂CH₃

I-2-88 — CH₂ O OCH₃

(2)Cl (4)Cl

I-2-89 — CH₂ O OCH₃

(2)Cl (4)Cl

I-2-90 — CH₂ O OCH₃

(2)Cl (4)SO₂CH₃

I-2-91 — CH₂ O OCH₃

(2)Cl (4)SO₂CH₃

I-2-92 — CH₂ O H N(CH₃)₂ (2)Cl (4)SO₂CH₃

I-2-93 — CH₂ O H N(CH₃)₂ (2)Cl (4)SO₂CH₃

I-2-94 — CH₂ O H

(2)Cl (4)SO₂CH₃

I-2-95 — CH₂ O H

(2)Cl (4)SO₂CH₃

I-2-96 — CH₂ O

(2)Cl (4)SO₂CH₃

I-2-97 — CH₂ O

(2)Cl (4)SO₂CH₃

I-2-98 — CH₂ O

NHCH₃ (2)Cl (4)SO₂CH₃

I-2-99 — CH₂ O

NHCH₃ (2)Cl (4)SO₂CH₃

I-2-100 — CH₂ O

NH₂ (2)Cl (4)SO₂CH₃

I-2-101 — CH₂ O

NH₂ (2)Cl (4)SO₂CH₃

I-2-102 — CH₂ O

N(CH₃)₂ (2)Cl (4)SO₂CH₃

I-2-103 — CH₂ O

N(CH₃)₂ (2)Cl (4)SO₂CH₃

I-2-104 — CH₂ O CH₃ NHC₂H₅ (2)Cl (4)SO₂CH₃

I-2-105 — CH₂ O CH₃ NHCH₃ (2)Cl (4)SO₂CH₃

I-2-106 — CH₂ O H

(2)Cl (4)SO₂CH₃

I-2-107 — CH₂ O H

(2)Cl (4)SO₂CH₃

I-2-108 — CH₂ O H

(2)Cl (4)SO₂CH₃

I-2-109 — CH₂ O H

(2)Cl (4)SO₂CH₃

I-2-110 — CH₂ O H

(2)Cl (4)SO₂CH₃

I-2-111 — CH₂ O H

(2)Cl (4)SO₂CH₃

I-2-112 — CH₂ O

NHCH₃ (2)Cl (4)SO₂CH₃

I-2-113 — CH₂ O

NHCH₃ (2)Cl (4)SO₂CH₃

I-2-114 — CH₂ O

N(CH₃)₂ (2)Cl (4)SO₂CH₃

I-2-115 — CH₂ O

N(CH₃)₂ (2)Cl (4)SO₂CH₃

I-2-116 — CH₂ O H NH₂ (2)Cl (4)SO₂CH₃

I-2-117 — CH₂ O H NH₂ (2)Cl (4)SO₂CH₃

I-2-118 O (CH₂)₂ O H NH₂ (2)Cl (4)Cl

log P = 1.66^(a)) I-2-119 O (CH₂)₂ O H NH₂ (2)Cl (4)Cl

log P = 1.22^(a)) I-2-120 — CH₂ O OCH₃ NH₂ (2)Cl (4)Cl

I-2-121 — CH₂ O OCH₃ NH₂ (2)Cl (4)Cl

I-2-122 — CH₂ O OCH₃ NH₂ (2)Cl (4)SO₂CH₃

I-2-123 — CH₂ O OCH₃ NH₂ (2)Cl (4)SO₂CH₃

I-2-124 — CH₂ O OCH₃ NHCH₃ (2)Cl (4)Cl

I-2-125 — CH₂ O OCH₃ NHCH₃ (2)Cl (4)Cl

I-2-126 — CH₂ O OCH₃ NHCH₃ (2)Cl (4)SO₂CH₃

I-2-127 — CH₂ O OCH₃ NHCH₃ (2)Cl (4)SO₂CH₃

I-2-128 — CH₂ O OCH₃ N(CH₃)₂ (2)Cl (4)Cl

I-2-129 — CH₂ O OCH₃ N(CH₃)₂ (2)Cl (4)Cl

I-2-130 — CH₂ O OCH₃ N(CH₃)₂ (2)Cl (4)SO₂CH₃

I-2-131 — CH₂ O OCH₃ N(CH₃)₂ (2)Cl (4)SO₂CH₃

I-2-132 — CH₂ O OCH₃

(2)Cl (4)Cl

I-2-133 — CH₂ O OCH₃

(2)Cl (4)Cl

I-2-134 — CH₂ O OCH₃

(2)Cl (4)SO₂CH₃

I-2-135 — CH₂ O OCH₃

(2)Cl (4)SO₂CH₃

I-2-136 — CH₂ O OCH₃

(2)Cl (4)Cl

I-2-137 — CH₂ O OCH₃

(2)Cl (4)Cl

I-2-138 — CH₂ O OCH₃

(2)Cl (4)SO₂CH₃

I-2-139 — CH₂ O OCH₃

(2)Cl (4)SO₂CH₃

I-2-140 — CH₂ O H

(2)Cl (4)SO₂CH₃

log P = 2.35^(a)) I-2-141 O (CH₂)₂ O H CH₃ (2)Cl (4)SO₂CH₃

I-2-142 O (CH₂)₂ O H CH₃ (2)Cl (4)SO₂CH₃

I-2-143 O (CH₂)₂ O H C₂H₅ (2)Cl (4)SO₂CH₃

I-2-144 O (CH₂)₂ O H C₂H₅ (2)Cl (4)SO₂CH₃

I-2-145 O

O H CH₃ (2)Cl (4)Cl

I-2-146 O

O H CH₃ (2)Cl (4)Cl

I-2-147 O

O H C₂H₅ (2)Cl (4)Cl

I-2-148 O

O H C₂H₅ (2)Cl (4)Cl

I-2-149 O

O H CH₃ (2)Cl (4)SO₂CH₃

I-2-150 O

O H CH₃ (2)Cl (4)SO₂CH₃

I-2-151 O

O H C₂H₅ (2)Cl (4)SO₂CH₃

I-2-152 O

O H C₂H₅ (2)Cl (4)SO₂CH₃

TABLE 2 Examples of compounds of the formula (I-3) (I-3)

Ex. (position) (position) No. A¹ A² Q R¹ R² X Y Z Physical data I-3-1 —CH₂ O H NH—NO₂ (2)NO₂ —

m.p.: 191° C. I-3-2 — CH₂ O CH₃ NHCH₃ (2)NO₂ —

I-3-3 — CH₂ O C₂H₅ NHC₂H₅ (2)NO₂ —

I-3-4 — (CH₂)₂ O H CH₃ (2)NO₂ —

I-3-5 — CH₂ O C₃H₇-i

(2)NO₂ —

log P = 2.53^(a)) I-3-6 — CH₂ O C₃H₇-i

(2)NO₂ —

log P = 1.64^(a)) I-3-7 — CH₂ O C₃H₇-i N(CH₃)₂ (2)NO₂ —

log P = 1.63^(a)) I-3-8 — CH₂ O

NHC₂H₅ (2)NO₂ —

log P = 2.60^(a)) I-3-9 — CH₂ O

NHC₂H₅ (2)NO₂ —

log P = 1.75^(a)) I-3-10 — CH₂ O

(2)NO₂ —

log P = 2.94^(a)) I-3-11 — CH₂ O

(2)NO₂ —

log P = 2.05^(a)) I-3-12 — CH₂ O H N(CH₃)₂ (2)NO₂ —

I-3-13 — CH₂ O H N(CH₃)₂ (2)NO₂ —

I-3-14 — CH₂ O H

(2)NO₂ —

I-3-15 — CH₂ O H

(2)NO₂ —

I-3-16 — CH₂ O

(2)NO₂ —

I-3-17 — CH₂ O

(2)NO₂ —

I-3-18 — CH₂ O

NHCH₃ (2)NO₂ —

I-3-19 — CH₂ O

NHCH₃ (2)NO₂ —

I-3-20 — CH₂ O

NH₂ (2)NO₂ —

I-3-21 — CH₂ O

NH₂ (2)NO₂ —

I-3-22 — CH₂ O

N(CH₃)₂ (2)NO₂ —

I-3-23 — CH₂ O

N(CH₃)₂ (2)NO₂ —

I-3-24 — CH₂ O CH₃ NHC₂H₅ (2)NO₂ —

I-3-25 — CH₂ O CH₃ NHCH₃ (2)NO₂ —

log P = 0.68^(a)) I-3-26 — CH₂ O H

(2)NO₂ —

I-3-27 — CH₂ O H

(2)NO₂ —

I-3-28 — CH₂ O H

(2)NO₂ —

I-3-29 — CH₂ O H

(2)NO₂ —

I-3-30 — CH₂ O H

(2)NO₂ —

I-3-31 — CH₂ O H

(2)NO₂ —

I-3-32 — CH₂ O

NHCH₃ (2)NO₂ —

I-3-33 — CH₂ O

NHCH₃ (2)NO₂ —

I-3-34 — CH₂ O

N(CH₃)₂ (2)NO₂ —

I-3-35 — CH₂ O

N(CH₃)₂ (2)NO₂ —

I-3-36 — CH₂ O H NH₂ (2)NO₂ —

I-3-37 — CH₂ O H NH₂ (2)NO₂ —

I-3-38 — CH₂ O CH₃ NHC₂H₅ (2)NO₂ —

I-3-39 — CH₂ O C₃H₇-i

(2)NO₂ —

log P = 3.53^(a)) I-3-40 — CH₂ O C₃H₇-i

(2)NO₂ —

log P = 2.59^(a)) I-3-41 — CH₂ O C₃H₇-i OC₂H₅ (2)NO₂ —

log P = 3.04^(a)) I-3-42 — CH₂ O C₃H₇-i OC₂H₅ (2)NO₂ —

log P = 2.06^(a)) I-3-43 — CH₂ O H OC₂H₅ (2)NO₂ —

I-3-44 — CH₂ O H OC₂H₅ (2)NO₂ —

I-3-45 — CH₂ O H OC₃H₇-i (2)NO₂ —

I-3-46 — CH₂ O H OC₃H₇-i (2)NO₂ —

I-3-47 — CH₂ O CH₃ OC₂H₅ (2)NO₂ —

I-3-48 — CH₂ O CH₃ OC₂H₅ (2)NO₂ —

I-3-49 — CH₂ O H NHOCH₃ (2)NO₂ —

I-3-50 — CH₂ O H NHOCH₃ (2)NO₂ —

I-3-51 — CH₂ O H N(CH₃)OCH₃ (2)NO₂ —

I-3-52 — CH₂ O H N(CH₃)OCH₃ (2)NO₂ —

I-3-53 — CH₂ O C₃H₇-i

(2)CF₃ —

I-3-54 — CH₂ O C₃H₇-i

(2)CF₃ —

I-3-55 — CH₂ O C₃H₇-i

(2)CF₃ —

I-3-56 — CH₂ O C₃H₇-i

(2)CF₃ —

I-3-57 — CH₂ O H N(CH₃)₂ (2)CF₃ —

I-3-58 — CH₂ O H N(CH₃)₂ (2)CF₃ —

I-3-59 — CH₂ O H

(2)CF₃ —

I-3-60 — CH₂ O H

(2)CF₃ —

I-3-61 — CH₂ O H

(2)CF₃ —

I-3-62 — CH₂ O H

(2)CF₃ —

I-3-63 — CH₂ O H

(2)CF₃ —

I-3-64 — CH₂ O H

(2)CF₃ —

I-3-65 — CH₂ O H

(2)CF₃ —

I-3-66 — CH₂ O H

(2)CF₃ —

I-3-67 — CH₂ O H

(2)CF₃ —

I-3-68 — CH₂ O H

(2)CF₃ —

I-3-69 — CH₂ O H

(2)CF₃ —

I-3-70 — CH₂ O H

(2)CF₃ —

I-3-71 — CH₂ O H OC₂H₅ (2)CF₃ —

I-3-72 — CH₂ O H OC₂H₅ (2)CF₃ —

I-3-73 — CH₂ O C₃H₇-i

(2)CF₃ —

I-3-74 — CH₂ O C₃H₇-i

(2)CF₃ —

I-3-75 — CH₂ O C₃H₇-i OC₂H₅ (2)CF₃ —

I-3-76 — CH₂ O C₃H₇-i OC₂H₅ (2)CF₃ —

I-3-77 — CH₂ O H OC₂H₅ (2)CF₃ —

I-3-78 — CH₂ O H OC₂H₅ (2)CF₃ —

I-3-79 — CH₂ O H OC₃H₇-i (2)CF₃ —

I-3-80 — CH₂ O H OC₃H₇-i (2)CF₃ —

I-3-81 — CH₂ O CH₃ OC₂H₅ (2)CF₃ —

I-3-82 — CH₂ O CH₃ OC₂H₅ (2)CF₃ —

I-3-83 — CH₂ O H NHOCH₃ (2)CF₃ —

I-3-84 — CH₂ O H NHOCH₃ (2)CF₃ —

I-3-85 — CH₂ O H N(CH₃)OCH₃ (2)CF₃ —

I-3-86 — CH₂ O H N(CH₃)OCH₃ (2)CF₃ —

I-3-87 — CH₂ O

NHCH₃ (2)CF₃ —

I-3-88 — CH₂ O

NHCH₃ (2)CF₃ —

I-3-89 — CH₂ O

N(CH₃)₂ (2)CF₃ —

I-3-90 — CH₂ O

N(CH₃)₂ (2)CF₃ —

I-3-91 — CH₂ O

OC₂H₅ (2)CF₃ —

I-3-92 — CH₂ O

OC₂H₅ (2)CF₃ —

I-3-93 — CH₂ O CH₃ NHCH₃ (2)CF₃ —

I-3-94 — CH₂ O CH₃ NHCH₃ (2)CF₃ —

I-3-95 — CH₂ O CH₃ N(CH₃)₂ (2)CF₃ —

I-3-96 — CH₂ O CH₃ N(CH₃)₂ (2)CF₃ —

Log P values given in the tables were determined in accordance with EECDirective 79/831 Annex V.A8 by HPLC (High Performance LiquidChromatography) using a reversed-phase column (C 18). Temperature: 43°C.

(a) Mobile phases for the determination in the acidic range: 0.1%aqueous phosphoric acid, acetonitrile; linear gradient from 10%acetonitrile to 90% acetonitrile—the corresponding measurement resultsin Tables 1 and 2 are labelled a).

(b) Mobile phases for the determination in the neutral range: 0.01 molaraqueous phosphate buffer solution, acetonitrile; linear gradient from10% acetonitrile to 90% acetonitrile—the corresponding measurementresults in Tables 1 and 2 are labelled b).

Calibration was carried out using unbranched alkane-2-ones (having 3 to16 carbon atoms) with known log P values (determination of the log Pvalues by the retention times using linear interpolation between twosuccessive alkanones).

The lambda max values were determined in the maxima of thechromatographic signals using the UV spectra from 200 nm to 400 nm.

Starting Materials of the Formula (II):

Example (II-1)

Step 1

11.7 g (85.1 mmol) of potassium carbonate and, after 15 min, 11.0 g(46.9 mmol) of 2-chloro-ethanol tosylate are added to a solution of 10.0g (42.5 mmol) of ethyl 2,4-dichloro-3-hydroxy-benzoate in 100 ml ofacetonitrile. The reaction mixture is stirred at 70° C. for 19 hoursand, after cooling, concentrated under reduced pressure, and 50 ml ofwater and 50 ml of dichloromethane are added to the residue. The organicphase is separated off, washed with water and saturated aqueous sodiumchloride solution, dried over sodium sulphate and filtered. From thefiltrate, the solvent is carefully distilled off under reduced pressure.

This gives 12.1 g (95% of theory) of ethyl2,4-dichloro-3-(2-chloro-ethoxy)-benzoate as an oil.

log P=3.76

Step 2

A solution of 2.2 g (55.0 mmol) of sodium hydroxide in 40 ml of water isadded to a solution of 10.0 g (33.6 mmol) of ethyl2,4-dichloro-3-(2-chloro-ethoxy)-benzoate in 70 ml of ethanol. Thereaction mixture is stirred at room temperature (about 20° C.) for 90minutes, and most of the ethanol is removed by evaporation under reducedpressure. The residue is adjusted to pH 1 using conc. hydrochloric acidand extracted with ethyl acetate. The organic phase is separated off,washed with saturated aqueous sodium chloride solution, dried oversodium sulphate and filtered. From the filtrate, the solvent iscarefully distilled off under reduced pressure.

This gives 9.0 g (99% of theory) of2,4-dichloro-3-(2-chloro-ethoxy)-benzoic acid as a white solid.

log P=2.31

Step 3

A solution of 8.5 g (31.5 mmol) of2,4-dichloro-3-(2-chloro-ethoxy)-benzoic acid in 12 ml of thionylchloride is heated at 60° C. for 1 hour. After the evolution of gas hasceased, the excess thionyl chloride is removed under reduced pressure.

This gives 9.0 g (99% of theory) of2,4-dichloro-3-(2-chloro-ethoxy)-benzoyl chloride as an oily residue.

Step 4

9.5 g of (94 mmol) of triethylamine, 9 g (31.3 mmol) of2,4-dichloro-3-(2-chloro-ethoxy)-benzoyl chloride and 5 drops ofN,N-dimethylformamide are added successively to a solution of 3.5 g(31.3 mmol) of 1-ethyl-5-hydroxy-1H-pyrazole in 200 ml ofdichloromethane. The reaction mixture is stirred at room temperature(about 20° C.), for 21 hours and then washed with 2N hydrochloric acidand saturated aqueous sodium chloride solution, dried over sodiumsulphate and filtered. From the filtrate, the solvent is removed underreduced pressure.

The oily residue is dissolved in 200 ml of acetonitrile, 17 g (168 mmol)of triethylamine and 3.26 g (38 mmol) of2-hydroxy-2-methyl-propionitrile are added and the mixture is stirred atroom temperature for another 20 hours. Most of the solvent is thenremoved under reduced pressure and the oily residue is taken up in 100ml of dichloromethane. The organic phase is washed with 2N hydrochloricacid and with saturated aqueous sodium chloride solution, dried oversodium sulphate and filtered. The filtrate is freed from the solventunder reduced pressure.

This gives 11.1 g (98% of theory) of[2,4-dichloro-3-(2-chloro-ethoxy)-phenyl]-(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-methanoneas an orange-yellow crystalline solid.

log P=2.73.

Step 5

A solution of 8.0 g (22 mmol) of[2,4-dichloro-3-(2-chloro-ethoxy)-phenyl]-(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-methanonein 150 ml of tetrahydrofuran and 200 ml of ammonia is heated in anautoclave at 90° C. for 6.5 hours. Most of the excess ammonia isevaporated off and the product that settles out is removed by filtrationand dried under reduced pressure.

This gives 4.3 g (57% of theory) of[3-(2-amino-ethoxy)-2,4-dichloro-phenyl]-(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-methanoneas a light-yellow crystalline solid.

log P=0.72.

Analogously to Example (II-1), it was also possible to prepare, forexample, the compounds of the general formula (II) listed in Table 3below.

TABLE 3 Examples of compounds of the formula (II) Ex. (position)(position) (position) No. —A¹—A²—NHR¹ X Y Z 11-2

(2) Cl (4) Cl

11-3

(2) Cl (4)SO₂CH₃

11-4

(2) Cl (4) Cl

11-5

(2) Cl (4)SO₂CH₃

11-6

(2) Cl (4) Cl

11-7

(2) Cl (4)SO₂CH₃

11-8

(2) Cl (4) Cl

Starting Materials of the Formula (IV):

Example (IV-1)

Step 1

At room temperature (about 20° C.) 15 g (59 mmol) of methyl2,4-dichloro-3-bromomethyl-benzoate and then 7.5 g (77 mmol) ofpotassium thiocyanate are introduced into 60 ml of acetonitrile. Thereaction mixture is slowly heated to reflux and then stirred at thistemperature under reflux for 20 hours. After cooling to roomtemperature, the solvent is stripped off under reduced pressure and theresidue is stirred with 70 ml of diethyl ether. Undissolved componentsare filtered off with suction, the solvent is removed under reducedpressure and the residue is distilled under reduced pressure.

This gives 2.7 g (17% of theory) of methyl2,4-dichloro-3-isocyanatomethyl-benzoate as an oil which is reactedfurther without further purification.

Step 2

5.6 g of crude methyl 2,4-dichloro-3-isocyanatomethyl-benzoate aredissolved in 20 ml of ethanol, and 1.2 g (20 mmol) of 2-propanamine areadded. The mixture is heated at the boil for 1 hour, the amount ofsolvent is reduced to one third of the original volume and the productis filtered off with suction.

This gives 1.7 g (9%, based on methyl 2,4-dichloro-3-methyl-benzoate) ofmethyl2,4-dichloro-3-[[[(isopropylamino)-thioxomethyl]-amino]-methyl]-benzoateas a solid (MS: M⁺=355, 2 Cl according to the isotope pattern).

Step 3

5 g (15 mmol) ofN-(3-methoxycarbonyl-2,6-dichloro-benzyl)-N′-isopropyl-thiourea aredissolved in 30 ml of methanol, and 10 ml (50 mmol) of a 30% strengthsolution of sodium methoxide in methanol are added. Over a period of 30minutes, 50 ml of water are added dropwise, and the mixture is then keptat 60° C. for 2 hours. Following neutralization with 2N hydrochloricacid, the product is filtered off with suction and dried.

This gives 4.4 g (91% of theory) of2,4-dichloro-3-[[[(isopropylamino)-thioxomethyl]-amino]-methyl]-benzoicacid as a solid of melting point>220° C.

Analogously to Example (IV-1), it is also possible to prepare, forexample, the compounds of the general formula (IVa) listed in Table 4below.

TABLE 4 Examples of compounds of the formula (IVa) Ex. No.

(position) X (position) Y R Physical Data IV-2

(2) Cl (4) Cl CH₃ log P = 0.89^(a)) IV-3

(2) Cl (4) Cl CH₃ m.p.: 195° C. IV-4

(2) Cl (4) Cl CH₃ m.p.: 140° C. IV-5

(2) Cl (4) Cl H m.p.: 175° C. IV-6

(2) Cl (4) Cl CH₃ m.p.: 81° C. IV-7

(2) NO₂ — CH₃ n_(D) ²⁰ = 1.5361 IV-8

(2) Cl (4) Cl H m.p. >260° C. IV-9

(2) Cl (4) Cl CH₃ m.p.: 76° C.  IV-10

(2) NO₂ — H m.p.: >220° C.  IV-11

(2) NO₂ — H m.p.: 210° C.  IV-12

(2) Cl (4) Cl CH₃ m.p.: 147° C.  IV-13

(2) Cl (4) Cl H m.p.: 173° C.

USE EXAMPLES Example A

Pre-emergence Test Solvent: 5 parts by weight of acetone Emulsifier: 1part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Seeds of the test plants are sown in normal soil. After 24 hours, thesoil is sprayed with the preparation of active compound such that theparticular amount of active compound desired is applied per unit area.The concentration of active compound in the spray liquor is chosen suchthat the particular amount of active compound desired is applied in 1000litres of water per hectare.

After three weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control. Thefigures denote:

-   -   0%=no effect (like untreated control)    -   100%=total destruction

In this test, for example, the compounds of Preparation Examples(I-2-1), (I-2-3), (I-2-5) and (I-2-6) exhibit strong activity againstweeds, and some are tolerated well by crop plants, such as, for example,maize, soya beans and wheat.

Example B

Post-emergence Test Solvent: 5 part by weight of acetone Emulsifier: 1part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Test plants of a height of 5-15 cm are sprayed with the preparation ofactive compound such that the particular amounts of active compounddesired are applied per unit area. The concentration of the spray liquoris chosen such that the particular amounts of active compound desiredare applied in 1000 l of water/ha.

After three weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control. Thefigures denote:

-   -   0%=no effect (like untreated control)    -   100%=total destruction

In this test, for example, the compounds of Preparation Examples(I-2-1), (I-2-3), (I-2-4), (I-2-5), (I-2-6), (I-2-7) and (I-2-8) exhibitstrong some are tolerated well by crop plants, such as, for example,maize, oilseed rape and wheat.

1. Compounds of the formula (I)

in which A¹ represents a single bond or represents O, S, SO, SO₂, A²represents alkanediyl (alkylene), alkenediyl or alkinediyl, Q representsO (oxygen), R¹ represents hydrogen or represents in each case optionallysubstituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl,alkylamino, dialkylamino, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl,aryl or arylalkyl, or represents the grouping —C(Q)-R², R² cyclopropyl,X represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl,halogen, or represents in each case optionally substituted alkyl,alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino,dialkylamino or dialkylaminosulphonyl, Y represents hydrogen, nitro,cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents ineach case optionally substituted alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino ordialkylaminosulphonyl, and Z represents


2. Compounds of the formula (I) according to claim 1, characterized inthat A¹ represents O or represents a single bond, A² representsalkanediyl (alkylene), alkenediyl or alkinediyl having in each case upto 6 carbon atoms, Q represents O (oxygen), R¹ represents hydrogen,represents in each case optionally cyano-, halogen-, C₁–C₄-alkoxy-,C₁–C₄-alkylthio-, C₁–C₄-alkylsulphinyl- orC₁–C₄-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl or alkylamino having in each case 1 to 6carbon atoms in the alkyl groups, represents dialkylamino having in eachcase 1 to 4 carbon atoms in the alkyl groups, represents in each caseoptionally cyano- or halogen-substituted alkenyl or alkinyl having ineach case 2 to 6 carbon atoms, represents in each case optionallycyano-, halogen- or C₁–C₄-alkyl-substituted cycloalkyl orcycloalkylalkyl having in each case 3 to 6 carbon atoms in thecycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety,represents in each case optionally nitro-, cyano-, halogen-,C₁–C₄-alkyl-, C₁–C₄-halogenoalkyl-, C₁–C₄-alkoxy- orC₁–C₄-halogenoalkoxy-substituted aryl or arylalkyl having in each case 6or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atomsin the alkyl moiety, or represents the grouping —C(Q)-R², R²cyclopropyl, (C═O), thioxo (C═S), imino (C═NH), cyanoimino (C═N—CN) andnitroimino (C═N—NO₂), X represents hydrogen, nitro, cyano, carboxyl,carbamoyl, thiocarbamoyl, halogen, or represents in each case optionallycyano-, halogen-, C₁–C₄-alkoxy-, C₁–C₄-alkylthio-, C₁–C₄-alkylsulphinyl-or C₁–C₄-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino ordialkylaminosulphonyl having in each case 1 to 6 carbon atoms in thealkyl groups, Y represents hydrogen, nitro, cyano, carboxyl, carbamoyl,thiocarbamoyl, halogen, or represents in each case optionally cyano-,halogen-, C₁–C₄-alkoxy-, C₁–C₄-alkylthio-, C₁–C₄-alkylsulphinyl- orC₁–C₄-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino ordialkylaminosulphonyl having in each case 1 to 6 carbon atoms in thealkyl groups, Z represents


3. Compounds of the formula (I) according to claim 1, characterized inthat A² represents methylene (—CH₂—), ethane-1,1-diyl (—CH(CH₃)—),ethane-1,2-diyl (dimethylene, —CH₂CH₂—), propane-1,1-diyl (—CH(C₂H₅)—),propane-1,2-diyl (—CH(CH₃)CH₂—), propane-1,3-diyl (—CH₂CH₂CH₂—),butane-1,3-diyl (—CH(CH₃)CH₂CH₂—), butane-1,4-diyl (—CH₂CH₂CH₂CH₂—),ethenediyl, propenediyl, butenediyl, ethinediyl, propinediyl orbutinediyl, R¹ represents hydrogen, represents in each case optionallycyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- ori-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-,methylsulphonyl- or ethylsulphonyl-substituted methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy,ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio,n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl,ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl,ethylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s-or t-butylamino, represents dimethylamino or diethylamino, represents ineach case optionally fluorine-, chlorine- and/or bromine-substitutedethenyl, propenyl, butenyl, pentenyl, ethinyl, propinyl, butinyl orpentinyl, represents in each case optionally cyano-, fluorine-,chlorine-, bromine-, methyl-, ethyl- or propyl-substituted cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl,cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or representsin each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-,methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-,trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-or trifluoromethoxy-substituted phenyl, naphthyl, phenylmethyl,phenylethyl, naphthylmethyl or naphthylethyl or represents the grouping—C(Q)-R², R² cyclopropyl morpholinyl, morpholinylamino, piperazinyl,pyridinyl, pyridinyloxy, pyridinylamino, pyridinylmethyl,pyridinylmethoxy, pyrimidinyl, pyrimidinyloxy, pyrimidinylmethyl,pyrimidinylmethoxy, X represents hydrogen, nitro, cyano, carboxyl,carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, orrepresents in each case optionally cyano-, fluorine-, chlorine-,methoxy-, ethoxy-, methylthio-, ethylthio-, methylsulphinyl-,ethylsulphinyl-, methylsulphonyl- or ethylsulphonyl-substituted methyl,ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- ori-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- ori-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl,ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl,ethylsulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- ori-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino,dimethylaminosulphonyl or diethylaminosulphonyl, Y represents hydrogen,nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine,bromine, iodine, or represents in each case optionally cyano-,fluorine-, chlorine-, methoxy-, ethoxy-, methylthio-, ethylthio-,methylsulphinyl-, ethylsulphinyl-, methylsulphonyl- orethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, R¹⁰ representshydrogen, represents in each case optionally cyano-, fluorine-,chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl,n- or i-propyl, n-, i-, s- or t-butyl, or represents in each caseoptionally cyano-, fluorine-, chlorine-, methyl- or ethyl-substitutedcyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, and R¹¹ representshydrogen, cyano, carbamoyl, fluorine, chlorine or bromine or representsin each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-,n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl,ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- ori-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl orethylsulphonyl.
 4. Compounds of the formula (I) according to claim 1,characterized in that A² represents methylene (—CH₂—), ethane-1,2-diyl(dimethylene, —CH₂CH₂—) or propane-1,3-diyl (—CH₂CH₂CH₂—), R¹ representshydrogen, represents in each case optionally cyano-, fluorine-,chlorine-, methoxy-, ethoxy-, methylthio-, ethylthio-, methylsulphinyl-,ethylsulphinyl-, methylsulphonyl- or ethylsulphonyl-substituted methyl,ethyl, n- or i-propyl, n- or i-butyl, represents methoxy, ethoxy, n- ori-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino,ethylamino, n- or i-propylamino, represents dimethylamino, represents ineach case optionally fluorine- and/or chlorine-substituted propenyl,butenyl, ethinyl, propinyl or butinyl, represents in each caseoptionally cyano-, fluorine-, chlorine- or methyl-substitutedcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl,cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or representsin each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-,methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-,trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-or trifluoromethoxy-substituted phenyl, phenylmethyl or phenylethyl, orrepresents the grouping —C(Q)-R², R² cyclopropyl2-oxo-1,3-diazacyclohexyl, morpholinyl, piperazinyl, pyridinyl,pyridinylmethyl, pyrimidinyl, pyrimidinylmethyl, X represents hydrogen,nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- ori-propyl, difluoromethyl, trifluoromethyl, dichloromethyl,trichloromethyl, methoxymethyl, methylthiomethyl, methylsulphinylmethyl,methylsulphonylmethyl, methoxy, ethoxy, difluoromethoxy,trifluoromethoxy, methylthio, ethylthio, methylsulphinyl,ethylsulphinyl, methylsulphonyl, ethylsulphonyl ordimethylaminosulphonyl, Y represents hydrogen, nitro, cyano, fluorine,chlorine, bromine, iodine, methyl, ethyl, difluoromethyl,trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl,methylthiomethyl, methylsulphinylmethyl, or represents optionallyfluorine-, chlorine-, or methyl-substituted cyclopropyl, R¹⁰ representshydrogen, represents optionally fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, or representsoptionally fluorine-, chlorine- or methyl-substituted cyclopropyl, andR¹¹ represents hydrogen, cyano, fluorine, chlorine, bromine, orrepresents in each case optionally fluorine-, chlorine-, methoxy-, orethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- ori-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,methylthio, ethylthio, n- or i-propylthio, methylsulphinyl,ethylsulphinyl, methylsulphonyl or ethylsulphonyl.
 5. Compounds of theformula (I) according to claim 1, characterized in that R¹ representshydrogen, or represents in each case optionally fluorine-, chlorine-,methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, representsmethoxy or ethoxy or represents the grouping —C(Q)-R², R² cyclopropyl Xrepresents hydrogen, nitro, fluorine, chlorine, bromine, methyl, ethylor trifluoromethyl, Y represents hydrogen, nitro, cyano, fluorine,chlorine, bromine, iodine, methyl, ethyl, difluoromethyl,trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl,methylthiomethyl, methylsulphinylmethyl, methylsulphonylmethyl, methoxy,ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio,methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl ordimethylaminosulphonyl.
 6. Process for preparing compounds of theformula I according to claim 1, characterized in that (a) compounds ofthe general formula (II)

 in which A¹, A², R¹, X, Y and Z are as defined in claim 1, are reactedwith compounds of the general formula (III)

 in which Q and R² are as defined in claim 1 and Q¹ represents halogen,alkoxy, alkylthio, aryloxy or arylthio, or, if appropriate, withcorresponding iso(thio)cyanates if appropriate in the presence of one ormore reaction auxiliaries and if appropriate in the presence of one ormore diluents, or that (b) carboxylic acids of the general formula (IV)

 in which A¹, A², Q, R¹, R², X and Y are as defined in claim 1, orreactive derivatives thereof, such as, for example, corresponding acidhalides, acid cyanides or esters are reacted with compounds of thegeneral formula (V)H-Z  (V)  in which Z is as defined in claim 1, if appropriate in thepresence of a dehydrating agent and also, if appropriate in the presenceof one or more reaction auxiliaries and, if appropriate, in the presenceof one or more diluents, or that (c) substituted benzoyl ketones of thegeneral formula (Ia)

 in which A¹, A², Q, R¹, R², R¹⁰, X and Y are as defined in claim 1, arereacted with an orthoformic ester or with a N,N-dimethyl-formamideacetal or with a cyanoformic ester or with carbon disulphide and analkylating agent and subsequently with hydroxylamine or an acid adductthereof, if appropriate in the presence of one or more reactionauxiliaries and if appropriate in the presence of one or more diluents,or that (d) aryl ketones of the general formula (VI)

 in which A¹, A², Q, R¹, X, Y and Z are as defined in claim 1 and Q²represents halogen, alkoxy, alkylthio, aryloxy or arylthio, or, ifappropriate, corresponding iso(thio)cyanates are reacted with compoundsof the general formula (VII)H-R²  (VII)  in which R² is as defined in claim 1, if appropriate in thepresence of one or more reaction auxiliaries and if appropriate in thepresence of one or more diluents, and following the practice of theprocess (a), (b), (c) or (d), the resulting compounds of the generalformula (I) are, if appropriate, subjected to subsequent reactionsaccording to customary methods for conversion into other compounds ofthe general formula (I).
 7. Herbicidal compositions, characterized inthat they comprise at least one compound according to any of claims 1 to5 and customary extenders.
 8. Method for controlling undesirable plants,characterized in that at least one compound according to any of claims 1to 5 or a composition according to claim 7 is allowed to act on theundesirable plants and/or their habitat.